Organic electroluminescence device

ABSTRACT

An organic electroluminescence device includes: a pair of electrodes; and at least one organic layer including a light emitting layer, the light emitting layer being provided between the pair of electrodes, wherein at least one layer of the at least one organic layer contains a compound represented by formula (1): 
     
       
         
         
             
             
         
       
         
         
           
             wherein each of Z 11  and Z 12  independently represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring; R 11  represents a hydrogen atom or a substituent, provided that a plurality of R 11 s are the same or different; m represents an integer of 1 or more; and L 1  represents a single bond or an m-valent linking group and is linked to any one of C atoms in R 11 , Z 11  and Z 12 , provided that when m is 1, L 1  does not exist.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a luminescence device capable ofconverting electric energy into light to achieve light emission, inparticular to an organic electroluminescence device (luminescence deviceor EL device).

2. Description of the Related Art

An organic electroluminescence (EL) device is being watched as apromising display device because light emission with high brightness isobtained at a low voltage. A consumed electric power is an importantcharacteristic value of this organic electroluminescence device. Theconsumed electric power is expressed by a product of voltage andcurrent. When not only a voltage value necessary for obtaining desiredbrightness is lower, but a current value is smaller, the consumedelectric powder of the device can be made lower.

In recent years, high efficiency of the device is being advanced byusing a phosphorescent material. Iridium complexes, platinum complexesand so on are known as the phosphorescent material (see, for example,JP-A-2001-247859 and JP-A-2007-19462). However, a device in which highefficiency and high durability are compatible with each other has notbeen developed yet.

Also, there have been reported organic EL devices using, as a material,a compound having a nitrogen-containing heterocyclic ring intending toprovide a device with high efficiency and low voltage (see, for example,JP-A-2002-100476 and JP-A-2004-171808). However, higher efficiency anddriving at a lower voltage are being demanded.

On the other hand, though Journal of Chemical Society, 1939, pages 1945to 1956 describes a compound obtained by condensing anitrogen-containing heterocyclic ring with an aromatic heterocyclic ringor an aromatic hydrocarbon ring, it does not describe any applicationsthereof.

SUMMARY OF THE INVENTION

An object of the invention is to provide an electroluminescence devicehaving high luminous efficiency and capable of being driven at a lowvoltage. Another object of the invention is to provide a highlycondensed nitrogen-containing heterocyclic compound which is suitablyused therefor.

The foregoing problems have been attained by the following measures.

[1] An organic electroluminescence device, comprising:

a pair of electrodes; and

at least one organic layer including a light emitting layer, the lightemitting layer being provided between the pair of electrodes,

wherein at least one layer of the at least one organic layer contains acompound represented by formula (1):

wherein each of Z₁₁ and Z₁₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring;

R₁₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₁s are the same or different;

m represents an integer of 1 or more; and

L₁ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in R₁₁, Z₁₁ and Z₁₂, provided that when m is 1, L₁does not exist.

[2] The organic electroluminescence device as described in [1] above,

wherein the compound represented by formula (1) is a compoundrepresented by formula (2):

wherein Z₂₂ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring;

R₂₁ represents a hydrogen atom or a substituent, provided that aplurality of R₂₁s are the same or different;

each of A₂₁ to A₂₃ independently represents a nitrogen atom or C—R₂₂;

R₂₂ represents a hydrogen atom or a substituent, provided that aplurality of R₂₂s are the same or different;

m represents an integer of 1 or more; and

L₂ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in R₂₁, Z₂₂ and A₂₁ to A₂₃, provided that when mis 1, L₂ does not exist.

[3] The organic electroluminescence device as described in [1] above,

wherein the compound represented by formula (1) is a compoundrepresented by formula (3):

wherein Z₃₁ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring;

R₃₁ represents a hydrogen atom or a substituent, provided that aplurality of R₃₁s are the same or different;

each of A₃₁ to A₃₄ independently represents a nitrogen atom or C—R₃₂;

R₃₂ represents a hydrogen atom or a substituent, provided that aplurality of R₃₂s are the same or different;

m represents an integer of 1 or more; and

L₃ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in R₃₁, Z₃₁ and A₃₁ to A₃₄, provided that when mis 1, L₃ does not exist.

[4] The organic electroluminescence device as described in [2] or [3]above,

wherein the compound represented by formula (2) or (3) is a compoundrepresented by formula (4):

wherein R₄₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₁s are the same or different;

each of A₄₁ to A₄₇ independently represents a nitrogen atom or C—R₄₂;

R₄₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₂s are the same or different;

m represents an integer of 1 or more; and

L₄ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in R₄₁ and A₄₁ to A₄₇, provided that when m is 1,L₄ does not exist.

[5] The organic electroluminescence device as described in [1] above,

wherein the compound represented by formula (1) is a compoundrepresented by formula (5):

wherein each of Z₅₁ to Z₅₃ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring;

m represents an integer of 1 or more; and

L₅ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in Z₅₁ to Z₅₃, provided that when m is 1, L₅ doesnot exist.

[6] The organic electroluminescence device as described in [5] above,

wherein the compound represented by the formula (5) is a compoundrepresented by formula (6):

wherein each of Z₆₁ and Z₆₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring;

each of A₆₁ to A₆₃ independently represents a nitrogen atom or C—R₆₁;

R₆₁ represents a hydrogen atom or a substituent, provided that aplurality of R₆₁s are the same or different;

m represents an integer of 1 or more; and

L₆ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in Z₆₁, Z₆₂ and A₆₁ to A₆₃, provided that when mis 1, L₆ does not exist.

[7] The organic electroluminescence device as described in [5] above,

wherein the compound represented by formula (5) is a compoundrepresented by formula (7):

wherein each of Z₇₁ and Z₇₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring;

each of A₇₁ to A₇₄ independently represents a nitrogen atom or C—R₇₁;

R₇₁ represents a hydrogen atom or a substituent, provided that aplurality of R₇₁s are the same or different;

m represents an integer of 1 or more; and

L₇ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in Z₇₁, Z₇₂ and A₇₁ to A₇₄, provided that when mis 1, L₇ does not exist.

[8] The organic electroluminescence device as described in [6] above,wherein the compound represented by the formula (6) is a compoundrepresented by formula (8):

wherein Z₈₂ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring;

each of A₈₁ to A₈₇ independently represents a nitrogen atom or C—R₈₁;

R₈₁ represents a hydrogen atom or a substituent, provided that aplurality of R₈₁s are the same or different;

m represents an integer of 1 or more; and

L₈ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in Z₈₂ and A₈₁ to A₈₇, provided that when m is 1,L₈ does not exist.

[9] The organic electroluminescence device as described in [7] above,

wherein the compound represented by the formula (7) is a compoundrepresented by formula (9):

wherein Z₉₁ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring;

each of A₉₁ to A₉₈ independently represents a nitrogen atom or C—R₉₁;

R₉₁ represents a hydrogen atom or a substituent, provided that aplurality of R₉₁s are the same or different;

m represents an integer of 1 or more; and

L₉ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in Z₉₁ and A₉₁ to A₉₈, provided that when m is 1,L₉ does not exist.

[10] The organic electroluminescence device as described in [8] or [9]above,

wherein the compound represented by the formula (8) or (9) is a compoundrepresented by formula (10):

wherein each of A₁₀₁ to A₁₀₁₁ independently represents a nitrogen atomor C—R₁₀₁;

R₁₀₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₁s are the same or different;

m represents an integer of 1 or more; and

L₁₀ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in A₁₀₁ to A₁₀₁₁, provided that when m is 1, L₁₀does not exist.

[11] A compound represented by formula (4-1):

wherein each of X₄₁₁ and X₄₁₂ independently represents C—R₄₁₁;

R₄₁₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₁₁s are the same or different;

each of A₄₁₁ to A₄₁₇ independently represents a nitrogen atom or C—R₄₁₂;

R₄₁₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₁₂s are the same or different;

L₄₁ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in X₄₁₁, X₄₁₂ and A₄₁₁ to A₄₁₇;

when the linking group as L₄₁ is an aromatic hydrocarbon ring group oran aromatic heterocyclic group, a size of the ring is from a 5-memberedto 6-membered ring; and

m represents an integer of 2 or more.

[12] The compound as described in [11] above, which is a compoundrepresented by formula (4-2):

wherein each of X₄₂₁ and X₄₂₂ independently represents C—R₄₂₁;

R₄₂₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₂₁s are the same or different;

each of A₄₂₁ to A₄₂₇ independently represents a nitrogen atom or C—R₄₂₂;

R₄₂₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₂₂s are the same or different;

R₄₂₃ represents a hydrogen atom or a substituent, provided that aplurality of R₄₂₃s are the same or different;

m represents an integer of from 2 to 4; and

the silicon linking group is linked to any one of C atoms in X₄₂₁, X₄₂₂and A₄₂₁ to A₄₂₇.

[13] The compound as described in [11] above, which is a compoundrepresented by formula (4-3):

wherein each of X₄₃₁ and X₄₃₂ independently represents C—R₄₃₁;

R₄₃₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₃₁s are the same or different;

each of A₄₃₁ to A₄₃₇ independently represents a nitrogen atom or C—R₄₃₂;

R₄₃₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₃₂s are the same or different;

R₄₃₃ represents a hydrogen atom or a substituent, provided that aplurality of R₄₃₃s are the same or different;

m represents an integer of from 2 to 4; and

the carbon linking group is linked to any one of C atoms in X₄₃₁, X₄₃₂and A₄₃₁ to A₄₃₇.

[14] The compound as described in [11] above, which is a compoundrepresented by formula (4-4):

wherein each of X₄₄₁ and X₄₄₂ independently represents C—R₄₄₁;

R₄₄₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₄₁s are the same or different;

each of A₄₄₁ to A₄₄₇ independently represents a nitrogen atom or C—R₄₄₂;

R₄₄₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₄₂s are the same or different;

Ar₄₄ represents an aromatic hydrocarbon ring or an aromatic heterocyclicring, and a size of the ring is from 5-membered to 6-membered ring;

Ar₄₄ is linked to any one of C atoms in X₄₄₁, X₄₄₂ and A₄₄₁ to A₄₄₇;

R₄₄₃ represents a hydrogen atom or a substituent, provided that aplurality of R₄₄₃s are the same or different;

m represents an integer of 2 or more; and

n represents an integer of 0 or more.

[15] A compound represented by formula (4-5):

wherein each of X₄₅₁ and X₄₅₂ independently represents C—R₄₅₁;

R₄₅₁ represents a hydrogen atom or a substituent, provided that aplurality of C—R₄₅₁s are the same or different;

each of A₄₅₁ to A₄₅₇ independently represents a nitrogen atom or C—R₄₅₂;

R₄₅₂ represents a hydrogen atom or a substituent, provided that aplurality of R₄₅₂s are the same or different;

R₄₅₃ represents a hydrogen atom or a substituent, provided that aplurality of R₄₅₃s are the same or different;

n represents an integer of 1 or more; and

the silicon substituent is linked to any one of C atoms in X₄₅₁, X₄₅₂and A₄₅₁ to A₄₅₇.

[16] The compound as described in [11] above, which is a compoundrepresented by formula (10-1):

wherein each of A₁₀₁₁ to A₁₀₁₁₁ independently represents a nitrogen atomor C—R₁₀₁₁;

R₁₀₁₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₁₁ are the same or different;

L₁₀₁ represents a single bond or an m-valent linking group and is linkedto any one of C atoms in A₁₀₁₁ to A₁₀₁₁₁;

when the linking group as L₁₀₁ is an aromatic hydrocarbon ring group oran aromatic heterocyclic group, a size of the ring is from a 5-memberedto 6-membered ring; and

m represents an integer of 2 or more.

[17] The compound as described in [16] above, which is a compoundrepresented by formula (10-2):

wherein each of A₁₀₂₁ to A₁₀₂₁₁ independently represents a nitrogen atomor C—R₁₀₂₁;

R₁₀₂₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₂₁s are the same or different;

R₁₀₂₂ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₂₂s are the same or different;

m represents an integer of from 2 to 4; and

the silicon linking group is linked to any one of C atoms in A₁₀₂₁ toA₁₀₂₁₁.

[18] The compound as described in [16] above, which is a compoundrepresented by formula (10-3):

wherein each of A₁₀₃₁ to A₁₀₃₁₁ independently represents a nitrogen atomor C—R₁₀₃₁;

R₁₀₃₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₃₁s are the same or different;

R₁₀₃₂ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₃₂s are the same or different;

m represents an integer of from 2 to 4; and

the carbon linking group is linked to any one of C atoms in A₁₀₃₁ toA₁₀₃₁₁.

[19] The compound as described in [16] above, which is a compoundrepresented by formula (10-4):

wherein each of A₁₀₄₁ to A₁₀₄₁₁ independently represents a nitrogen atomor C—R₁₀₄₁;

R₁₀₄₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₄₁s are the same or different;

Ar₁₀₄ represents an aromatic hydrocarbon ring or an aromaticheterocyclic ring, and a size of the ring is from 5-membered to6-membered ring;

Ar₁₀₄ is linked to any one of C atoms in A₁₀₄₁ to A₁₀₄₁₁;

R₁₀₄₂ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₄₂s are the same or different;

m represents an integer of 2 or more; and

n represents an integer of 0 or more.

[20] A compound represented by formula (10-5):

wherein each of A₁₀₅₁ to A₁₀₅₁₁ independently represents a nitrogen atomor C—R₁₀₅₁;

R₁₀₅₁ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₅₁s are the same or different;

R₁₀₅₂ represents a hydrogen atom or a substituent, provided that aplurality of R₁₀₅₂s are the same or different;

n represents an integer of 1 or more; and

the silicon linking group is linked to any one of C atoms in A₁₀₅₁ toA₁₀₅₁₁.

[21] An organic electroluminescence device, comprising:

a pair of electrodes; and

at least one organic layer including a light emitting layer, the lightemitting layer being provided between the pair of electrodes,

wherein at least one layer of the at least one organic layer containsthe compound represented by any one of formulae (4-1) to (4-5) and(10-1) to (10-5) as described in [11] to [20] above.

[22] The organic electroluminescence device as described in any one of[1] to [10] and [21] above,

wherein the light emitting layer contains a phosphorescent material.

[23] The organic electroluminescence device as described in [22] above,

wherein the phosphorescent material is an iridium complex or a platinumcomplex.

[24] The organic electroluminescence device as described in any one of[1] to [10] and [21] to [23] above,

wherein the light emitting layer contains the compound represented byany one of formulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5).

[25] The organic electroluminescence device as described in any one of[1] to [10] and [21] to [24] above,

wherein the pair of electrodes includes an anode,

a hole transport layer is provided between the light emitting layer andthe anode, and

the hole transport layer contains the compound represented by any one offormulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5).

[26] The organic electroluminescence device as described in any one of[1] to [10] and [21] to [25] above,

wherein the pair of electrodes includes a cathode,

an electron transport layer is provided between the light emitting layerand the cathode, and

the electron transport layer contains the compound represented by anyone of formulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5).

[27] The organic electroluminescence device as described in any one of[1] to [10] and [21] to [26] above,

wherein a glass transition temperature of the compound represented byany one of formulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5) is130° C. or higher and not higher than 450° C.

[28] The organic electroluminescence device as described in any one of[1] to [10] and [21] to [27] above,

wherein a minimum excitation triplet energy level of the compoundrepresented by any one of the formulae (1) to (10), (4-1) to (4-5) and(10-1) to (10-5) is 60 kcal/mole (251.4 kJ/mole) or more and not morethan 95 kcal/mole (398.1 kJ/mole).

DETAILED DESCRIPTION OF THE INVENTION

The organic electroluminescence device of the invention is an organicelectroluminescence device comprising a pair of electrodes havingtherebetween at least one organic layer including a light emittinglayer, wherein a compound represented by the following formula (1) iscontained in at least one of the organic layers.

The compound represented by the formula (1) includes a partial structuredescribed below, and according to this structure, it becomes possible toattain high efficiency and low-voltage driving of the organicelectroluminescence device.

The compound represented by the formula (1) is a condensed heterocycliccompound in which at least four rings are condensed with each other.Since the thus highly condensed compound represented by the formula (1)is expanded with respect to conjugation as compared with existingnitrogen-containing heterocyclic compounds, it is able to enhanceelectron injection properties while keeping hole injection propertiesand to enhance a balance of the charge transfer in the organicelectroluminescence device. In particular, in the case where the lightemitting layer is in a hole-excess state, by using the compound of theinvention, the injection of an electron into the light emitting layerbecomes easy, the charge balance within the light emitting layer isimproved, and high efficiency and low-voltage driving of the organicelectroluminescence device may be realized.

[Compound Represented by the Formula (1)]

The compound represented by the formula (1) is described in detail.

In the formula (1), each of Z₁₁ and Z₁₂ independently represents anaromatic heterocyclic ring or an aromatic hydrocarbon ring; R₁₁represents a hydrogen atom or a substituent; each R₁₁ may be the same asor different from every other R₁₁; m represents an integer of 1 or more;and L₁ represents a single bond or an m-valent linking group and islinked to any one of C atoms in R₁₁, Z₁₁ and Z₁₂, provided that when mis 1, then L₁ does not exist.

As the substituent represented by R₁₁, those which are exemplified belowas the following group A of substituent are applicable.

(Group A of Substituent)

Examples of the group A of substituent include an alkyl group(preferably an alkyl group having from 1 to 30 carbon atoms, morepreferably an alkyl group having from 1 to 20 carbon atoms, andespecially preferably an alkyl group having from 1 to 10 carbon atoms;for example, a methyl group, an ethyl group, an isopropyl group, atert-butyl group, an n-octyl group, an n-decyl group, an n-hexadecylgroup, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group,etc.), an alicyclic hydrocarbon group (preferably an alicyclichydrocarbon group having from 1 to 30 carbon atoms, more preferably analicyclic hydrocarbon group having from 1 to 20 carbon atoms, andespecially preferably an alicyclic hydrocarbon group having from 1 to 10carbon atoms; for example, an adamantyl group, a cyclopropyl group, acyclopentyl group, a cyclohexyl group, etc.), an alkenyl group(preferably an alkenyl group having from 2 to 30 carbon atoms, morepreferably an alkenyl group having from 2 to 20 carbon atoms, andespecially preferably an alkenyl group having from 2 to 10 carbon atoms;for example, a vinyl group, an allyl group, a 2-butenyl group, a3-pentenyl group, etc.), an alkynyl group (preferably an alkynyl grouphaving from 2 to 30 carbon atoms, more preferably an alkynyl grouphaving from 2 to 20 carbon atoms, and especially preferably an alkynylgroup having from 2 to 10 carbon atoms; for example, a propargyl group,a 3-pentynyl group, etc.), an aryl group (preferably an aryl grouphaving from 6 to 30 carbon atoms, more preferably an aryl group havingfrom 6 to 20 carbon atoms, and especially preferably from 6 to 12 carbonatoms; for example, a phenyl group, a p-methylphenyl group, a naphthylgroup, an anthranyl group, etc.), an amino group (preferably an aminogroup having from 0 to 30 carbon atoms, more preferably an amino grouphaving from 0 to 20 carbon atoms, and especially preferably an aminogroup having from 0 to 10 carbon atoms; for example, an amino group, amethylamino group, a dimethylamino group, a diethylamino group, adibenzylamino group, a diphenylamino group, a ditolylamino group, etc.);an alkoxy group (preferably an alkoxy group having from 1 to 30 carbonatoms, more preferably an alkoxy group having from 1 to 20 carbon atoms,and especially preferably an alkoxy group having from 1 to 10 carbonatoms; for example, a methoxy group, an ethoxy group, a butoxy group, a2-ethylhexyloxy group, etc.), an aryloxy group (preferably an aryloxygroup having from 6 to 30 carbon atoms, an aryloxy group having from 6to 20 carbon atoms, and especially preferably an aryloxy group havingfrom 6 to 12 carbon atoms; for example, a phenyloxy group, a1-naphthyloxy group, a 2-naphthyloxy group, etc.), a heterocyclic oxygroup (preferably a heterocyclic oxy group having from 1 to 30 carbonatoms, more preferably a heterocyclic oxy group having from 1 to 20carbon atoms, and especially preferably a heterocyclic oxy group havingfrom 1 to 12 carbon atoms; for example, a pyridyloxy group, a pyrazyloxygroup, a pyrimidyloxy group, a quinolyloxy group, etc.), an acyl group(preferably an acyl group having from 1 to 30 carbon atoms, morepreferably an acyl group having from 1 to 20 carbon atoms, andespecially preferably an acyl group having from 1 to 12 carbon atoms;for example, an acetyl group, a benzoyl group, a formyl group, apivaloyl group, etc.), an alkoxycarbonyl group (preferably analkoxycarbonyl group having from 2 to 30 carbon atoms, more preferablyan alkoxycarbonyl group having from 2 to 20 carbon atoms, and especiallypreferably an alkoxycarbonyl group having from 2 to 12 carbon atoms; forexample, a methoxycarbonyl group, an ethoxycarbonyl group, etc.), anaryloxycarbonyl group (preferably an aryloxycarbonyl group having from 7to 30 carbon atoms, more preferably an aryloxycarbonyl group having from7 to 20 carbon atoms, and especially preferably an aryloxycarbonyl grouphaving from 7 to 12 carbon atoms; for example, a phenyloxycarbonylgroup, etc.), an acyloxy group (preferably an acyloxy group having from2 to 30 carbon atoms, more preferably an acyloxy group having from 2 to20 carbon atoms, and especially preferably an acyloxy group having from2 to 10 carbon atoms; for example, an acetoxy group, a benzoyloxy group,etc.), an acylamino group (preferably an acylamino group having from 2to 30 carbon atoms, more preferably an acylamino group having from 2 to20 carbon atoms, and especially preferably an acylamino group havingfrom 2 to 10 carbon atoms; for example, an acetylamino group, abenzoylamino group, etc.), an alkoxycarbonylamino group (preferably analkoxycarbonylamino group having from 2 to 30 carbon atoms, morepreferably an alkoxycarbonylamino group having from 2 to 20 carbonatoms, and especially preferably an alkoxycarbonylamino group havingfrom 2 to 12 carbon atoms; for example, a methoxycarbonylamino group,etc.), an aryloxycarbonylamino group (preferably an aryloxycarbonylaminogroup having from 7 to 30 carbon atoms, more preferably anaryloxycarbonylamino group having from 7 to 20 carbon atoms, andespecially preferably an aryloxycarbonylamino group having from 7 to 12carbon atoms; for example, a phenyloxycarbonylamino group, etc.), asulfonylamino group (preferably a sulfonylamino group having from 1 to30 carbon atoms, more preferably a sulfonylamino group having from 1 to20 carbon atoms, and especially preferably a sulfonylamino group havingfrom 1 to 12 carbon atoms; for example, a methanesulfonylamino group, abenzenesulfonylamino group, etc.), a sulfamoyl group (preferably asulfamoyl group having from 0 to 30 carbon atoms, more preferably asulfamoyl group having from 0 to 20 carbon atoms, and especiallypreferably a sulfamoyl group having from 0 to 12 carbon atoms; forexample, a sulfamoyl group, a methylsulfamoyl group, a dimethylsulfamoylgroup, a phenylsulfamoyl group, etc.), a carbamoyl group (preferably acarbamoyl group having from 1 to 30 carbon atoms, more preferably acarbamoyl group having from 1 to 20 carbon atoms, and especiallypreferably a carbamoyl group having from 1 to 12 carbon atoms; forexample, a carbamoyl group, a methylcarbamoyl group, a diethylcarbamoylgroup, a phenylcarbamoyl group, etc.), an alkylthio group (preferably analkylthio group having from 1 to 30 carbon atoms, more preferably analkylthio group having from 1 to 20 carbon atoms, and especiallypreferably an alkylthio group having from 1 to 12 carbon atoms; forexample, a methylthio group, an ethylthio group, etc.), an arylthiogroup (preferably an arylthio group having from 6 to 30 carbon atoms,more preferably an arylthio group having from 6 to 20 carbon atoms, andespecially preferably an arylthio group having from 6 to 12 carbonatoms; for example, a phenylthio group, etc.), a heterocyclic thio group(preferably a heterocyclic thio group having from 1 to 30 carbon atoms,more preferably a heterocyclic thio group having from 1 to 20 carbonatoms, and especially preferably a heterocyclic thio group having from 1to 12 carbon atoms; for example, a pyridylthio group, a2-benzimizolylthio group, a 2-benzoxazolylthio group, a2-benzthiazolylthio group, etc.), a sulfonyl group (preferably asulfonyl group having from 1 to 30 carbon atoms, more preferably asulfonyl group having from 1 to 20 carbon atoms, and especiallypreferably a sulfonyl group having from 1 to 12 carbon atoms; forexample, a mesyl group, a tosyl group, etc.), a sulfinyl group(preferably a sulfinyl group having from 1 to 30 carbon atoms, morepreferably a sulfinyl group having from 1 to 20 carbon atoms, andespecially preferably a sulfinyl group having from 1 to 12 carbon atoms;for example, a methanesulfinyl group, a benzenesulfinyl group, etc.), aureido group (preferably a ureido group having from 1 to 30 carbonatoms, more preferably a ureido group having from 1 to 20 carbon atoms,and especially preferably a ureido group having from 1 to 12 carbonatoms; for example, a ureido group, a methylureido group, a phenylureidogroup, etc.), a phosphoric acid amide group (preferably a phosphoricacid amide group having from 1 to 30 carbon atoms, more preferably aphosphoric acid amide group having from 1 to 20 carbon atoms, andespecially preferably a phosphoric acid amide group having from 1 to 12carbon atoms; for example, a diethylphosphoric acid amide group, aphenylphosphoric acid amide group, etc.), a hydroxyl group, a mercaptogroup, a halogen atom (for example, a fluorine atom, a chlorine atom, abromine atom, an iodine atom, etc.), a cyano group, a sulfo group, acarboxyl group, a nitro group, a hydroxamic acid group, a sulfino group,a hydrazino group, an imino group, a heterocyclic group (preferably aheterocyclic group having from 1 to 30 carbon atoms, and more preferablya heterocyclic group having from 1 to 12 carbon atoms; examples of thehetero atom include a nitrogen atom, an oxygen atom and a sulfur atom;and specific examples of the heterocyclic group include an imidazolylgroup, a pyridyl group, a quinolyl group, a furyl group, a thienylgroup, a piperidyl group, a morpholino group, a benzoxazolyl group, abenzimidazolyl group, a benzthiazolyl group, a carbazolyl group, anazepinyl group, etc.), a silyl group (preferably a silyl group havingfrom 3 to 40 carbon atoms, more preferably a silyl group having from 3to 30 carbon atoms, and especially preferably a silyl group having from3 to 24 carbon atoms; for example, a trimethylsilyl group, atriphenylsilyl group, etc.), a silyloxy group (preferably a silyloxygroup having from 3 to 40 carbon atoms, more preferably a silyloxy grouphaving from 3 to 30 carbon atoms, and especially preferably a silyloxygroup having from 3 to 24 carbon atoms; for example, a trimethylsilyloxygroup, a triphenylsilyloxy group, etc.) and a phosphoryl group (forexample, a diphenylphosphoryl group, a dimethylphosphoryl group, etc.).Each of these substituents may be further substituted. As the furthersubstituent, the groups selected among those in the foregoing group A ofsubstituent may be exemplified.

Also, a plurality of these substituents may be bound to each other toform a ring.

R₁₁s may be linked to each other to form a condensed ring. Examples ofthe ring which is formed include a benzene ring, a pyridine ring, apyrazine ring, a pyrimidine ring, a triazine ring, a pyridazine ring, apyrrole ring, a pyrazole ring, an imidazole ring, a triazole ring, anoxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, afuran ring, a thiophene ring, a selenophene ring, a silole ring, agermole ring and a phosphole ring. Of these, a benzene ring, a pyridinering, a furan ring, a thiophene ring, an imidazole ring, a thiazolering, an oxazole ring, a benzothiazole ring, a benzothiophene ring and abenzofuran ring are preferable; and a benzene ring, a pyridine ring, afuran ring, an oxazole ring and a benzofuran ring are more preferable.Each of these rings may be further substituted. As the furthersubstituent, the groups selected among those in the foregoing group A ofsubstituent may be exemplified.

R₁₁ is preferably a hydrogen atom, an alkyl group, an alicyclichydrocarbon group, an aryl group, a fluorine group, an amino group, analkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthiogroup, an arylthio group, a heterocyclic thio group, a cyano group, aheterocyclic group, a silyl group, a silyloxy group or a group capableof forming a condensed ring upon linking of R₁₁s each other; morepreferably a hydrogen atom, an alkyl group, an alicyclic hydrocarbongroup, an aryl group, a fluorine group, a cyano group, a silyl group ora heterocyclic group; further more preferably a hydrogen atom, an alkylgroup, an alicyclic hydrocarbon group, an aryl group, a fluorine group,a cyano group, a silyl group, a heterocyclic group or a group capable offorming a condensed ring upon linking of R₁₁s each other; still furthermore preferably an alkyl group, a silyl group, an alicyclic hydrocarbongroup, an aryl group, a heterocyclic group or a group capable forforming a benzene ring or a pyridine ring upon linking of R₁₁s eachother; especially preferably a methyl group, an ethyl group, anisopropyl group, a tert-butyl group, a trimethylsilyl group, atriphenylsilyl group, a phenyl group, a p-methylphenyl group, a naphthylgroup, an anthranyl group or a group capable for forming a benzene ringor a pyridine ring upon linking of R₁₁s each other; and most preferablya tert-butyl group, a trimethylsilyl group, a triphenylsilyl group, aphenyl group or a group capable for forming a benzene ring or a pyridinering upon linking of R₁₁s each other.

In the formula (1), examples of the aromatic heterocyclic ring and thearomatic hydrocarbon ring represented by each of Z₁₁ and Z₁₂ include afuran ring, a thiophene ring, a pyridine ring, a pyridazine group, apyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring,an oxadiazole ring, a triazole ring, an imidazole ring, a pyrazole ring,a thiazole ring, an oxazole ring, an indole ring, a benzimidazole ring,a benzothiazole ring, a benzoxazole ring, a quinoxaline ring, aquinazoline ring, a phthalazine ring, a carbazole ring, a carbolinering, a ring obtained by further substituting a carbon atom of ahydrocarbon ring constituting a carboline ring with a nitrogen atom, abenzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, ananthracene ring, a phenanthrene ring, a pyrene ring, a chrysene ring, anaphthacene ring, a triphenylene ring, an o-terphenyl ring, anm-terphenyl ring, a p-terphenyl ring, an acenaphthene ring, a coronenering, a fluorene ring, a fluoranthrene ring, a naphthacene ring, apentacene ring, a perylene ring, a pentaphene ring, a picene ring, apyrene ring, a pyranthrene ring, an anthranthrene ring and a benzofuranring.

Each of Z₁₁ and Z₁₂ is independently preferably a benzene ring, apyridine ring, a furan ring, a thiophene ring, an imidazole ring, athiazole ring, an oxazole ring, a benzothiazole ring, a benzothiophenering or a benzofuran ring; and more preferably a benzene ring, apyridine ring, a furan ring, an oxazole ring or a benzofuran ring.

Each of the aromatic heterocyclic ring and the aromatic hydrocarbon ringmay have a substituent. As the substituent, those which are exemplifiedpreviously as the group A of substituent are applicable. As thesubstituent, a methyl group, an ethyl group, an isopropyl group, atert-butyl group, a trimethylsilyl group, a triphenylsilyl group, aphenyl group, a p-methylphenyl group, a naphthyl group and an anthranylgroup are especially preferable; and a tert-butyl group, atrimethylsilyl group, a triphenylsilyl group and a phenyl group are themost preferable.

L₁ represents a single bond or an m-valent linking group. As them-valent linking group, linking groups constituted of at least one atomselected among a carbon atom, a nitrogen atom, an oxygen atom, a sulfuratom, a silicon atom, a germanium atom and a phosphorus atom arepreferable.

m represents an integer of 2 or more, preferably from 2 to 6, morepreferably from 2 to 4, further more preferably 2 or 3, and especiallypreferably 2.

L₁ is more preferably a single bond, a substituted or unsubstitutedcarbon atom, a substituted or unsubstituted nitrogen atom, a substitutedsilicon atom, a substituted germanium atom, an oxygen atom, a sulfuratom or a 5-membered to 6-membered aromatic hydrocarbon ring group oraromatic heterocyclic group; further more preferably a single bond, asubstituted or unsubstituted carbon atom, a substituted or unsubstitutednitrogen atom, a substituted silicon atom, a substituted germanium atomor a 5-membered to 6-membered aromatic hydrocarbon ring group; evenfurther more preferably a single bond, a substituted carbon atom, asubstituted silicon atom, a substituted nitrogen atom or a substitutedgermanium atom; and especially preferably a single bond, a carbon atomsubstituted with an alkyl group or a phenyl group, a silicon atom, agermanium atom or a nitrogen atom. If possible, such a linking group mayfurther have a substituent. As the substituent which may be introduced,those which are exemplified previously as the group A of substituent areapplicable.

When the linking group is an aromatic hydrocarbon ring group or anaromatic heterocyclic group, then a size of the ring is from a5-membered to 6-membered ring. This is for the purpose of keeping a highT₁ level (minimum excitation triplet energy level). Specific examples ofthe linking group are given below, but it should not be construed thatthe invention is limited thereto.

Of these, the following group (a-1) of linking group is preferable.

One of preferred embodiments as the compound represented by the formula(1) is concerned with a compound represented by the following formula(2).

In the formula (2), Z₂₂ represents an aromatic heterocyclic ring or anaromatic hydrocarbon ring; R₂₁ represents a hydrogen atom or asubstituent; each R₂₁ may be the same as or different from every otherR₂₁; each of A₂₁ to A₂₃ independently represents a nitrogen atom orC—R₂₂; R₂₂ represents a hydrogen atom or a substituent; each R₂₂ may bethe same as or different from every other R₂₂; m represents an integerof 1 or more; and L₂ represents a single bond or an m-valent linkinggroup and is linked to any one of C atoms in R₂₁, Z₂₂ and A₂₁ to A₂₃,provided that when m is 1, then L₂ does not exist.

In the formula (2), though a combination of A₂₁ to A₂₃ is notparticularly limited, a number of the nitrogen atom in A₂₁ to A₂₃ ispreferably from 0 to 2, and more preferably from 0 to 1. m, L₂, Z₂₂ andR₂₁ are respectively synonymous with m, L₁, Z₁₂ and R₁₁ in the formula(1), and preferred ranges thereof are also the same.

As the substituent represented by R₂₂, those which are exemplifiedpreviously as the group A of substituent are applicable.

Each R₂₂ may be the same as or different from every other R₂₂. Also, R₂₂may further have a substituent, and as the substituent, those which areexemplified previously as the group A of substituent are applicable.Also, R₂₂s may be linked to each other to form a condensed ring.Examples of the ring which is formed include a benzene ring, a pyridinering, a pyrazine ring, a pyrimidine ring, a triazine ring, a pyridazinering, a pyrrole ring, a pyrazole ring, an imidazole ring, a triazolering, an oxazole ring, an oxadiazole ring, a thiazole ring, athiadiazole ring, a furan ring, a thiophene ring, a selenophene ring, asilole ring, a germole ring and a phosphole ring.

R₂₂ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, a fluorine group, an amino group, an alkoxygroup, an aryloxy group, a heterocyclic oxy group, an alkylthio group,an arylthio group, a heterocyclic thio group, a cyano group, aheterocyclic group, a silyl group or a silyloxy group; more preferably ahydrogen atom, an alkyl group, an aromatic hydrocarbon ring group, afluorine group, a cyano group, a silyl group or a heterocyclic group;further more preferably an alkyl group, a silyl group, an aromatichydrocarbon ring group or an aromatic heterocyclic group; especiallypreferably a methyl group, an ethyl group, an isopropyl group, atert-butyl group, a trimethylsilyl group, a triphenylsilyl group, aphenyl group, a p-methylphenyl group, a naphthyl group or an anthranylgroup; and most preferably a tert-butyl group, a trimethylsilyl group, atriphenylsilyl group or a phenyl group.

One of preferred embodiments as the compound represented by the formula(1) is concerned with a compound represented by the following formula(3).

In the formula (3), Z₃₁ represents an aromatic heterocyclic ring or anaromatic hydrocarbon ring; R₃₁ represents a hydrogen atom or asubstituent; each R₃₁ may be the same as or different from every otherR₃₁; each of A₃₁ to A₃₄ independently represents a nitrogen atom orC—R₃₂; R₃₂ represents a hydrogen atom or a substituent; each R₃₂ may bethe same as or different from every other R₃₂; m represents an integerof 1 or more; and L₃ represents a single bond or an m-valent linkinggroup and is linked to any one of C atoms in R₃₁, Z₃₁ and A₃₁ to A₃₄,provided that when m is 1, then L₃ does not exist.

In the formula (3), though a combination of A₃₁ to A₃₄ is notparticularly limited, a number of the nitrogen atom in A₃₁ to A₃₄ ispreferably from 0 to 2, and more preferably from 0 to 1. m, L₃, Z₃₁ andR₃₁ are respectively synonymous with m, L₁, Z₁₁ and R₁₁ in the formula(1), and preferred ranges thereof are also the same.

R₃₂ is synonymous with R₂₂ in the formula (2), and a preferred rangethereof is also the same.

One of preferred embodiments as the compounds represented by theformulae (2) and (3) is concerned with a compound represented by thefollowing formula (4).

In the formula (4), R₄₁ represents a hydrogen atom or a substituent;each R₄₁ may be the same as or different from every other R₄₁; each ofA₄₁ to A₄₇ independently represents a nitrogen atom or C—R₄₂; R₄₂represents a hydrogen atom or a substituent; each R₄₂ may be the same asor different from every other R₄₂; m represents an integer of 1 or more;and L₄ represents a single bond or an m-valent linking group and islinked to any one of C atoms in R₄₁ and A₄₁ to A₄₇, provided that when mis 1, then L₄ does not exist.

In the formula (4), though a combination of A₄₁ to A₄₇ is notparticularly limited, a number of the nitrogen atom in A₄₁ to A₄₇ ispreferably from 0 to 4, and more preferably from 0 to 2.

m, L₄, R₄₁ and R₄₂ are respectively synonymous with m, L₂, R₂₁ and R₂₂in the formula (2), and preferred ranges thereof are also the same.

One of preferred embodiments as the compound represented by the formula(1) is concerned with a compound represented by the following formula(5).

In the formula (5), each of Z₅₁ to Z₅₃ independently represents anaromatic heterocyclic ring or an aromatic hydrocarbon ring; m representsan integer of 1 or more; and L₅ represents a single bond or an m-valentlinking group and is linked to any one of C atoms in Z₅₁ to Z₅₃,provided that when m is 1, then L₅ does not exist.

m, L₅ and Z₅₁ to Z₅₃ are respectively synonymous with m, L₁ and Z₁₁ toZ₁₂ in the formula (1), and preferred ranges thereof are also the same.

One of preferred embodiments as the compound represented by the formula(5) is concerned with a compound represented by the following formula(6).

In the formula (6), each of Z₆₁ and Z₆₂ independently represents anaromatic heterocyclic ring or an aromatic hydrocarbon ring; each of A₆₁to A₆₃ independently represents a nitrogen atom or C—R₆₁; R₆₁ representsa hydrogen atom or a substituent; each R₆₁ may be the same as ordifferent from every other R₆₁; m represents an integer of 1 or more;and L₆ represents a single bond or an m-valent linking group and islinked to any one of C atoms in Z₆₁, Z₆₂ and A₆₁ to A₆₃, provided thatwhen m is 1, then L₆ does not exist.

In the formula (6), though a combination of A₆₁ to A₆₃ is notparticularly limited, a number of the nitrogen atom in A₆₁ to A₆₃ ispreferably from 0 to 2, and more preferably from 0 to 1. m, L₆, Z₆₁ andZ₆₂ are respectively synonymous with m, L₅, Z₅₂ and Z₅₃ in the formula(5), and preferred ranges thereof are also the same.

R₆₁ is synonymous with R₂₂ in the formula (2), and a preferred rangethereof is also the same.

One of preferred embodiments as the compound represented by the formula(5) is concerned with a compound represented by the following formula(7).

In the formula (7), each of Z₇₁ and Z₇₂ independently represents anaromatic heterocyclic ring or an aromatic hydrocarbon ring; each of A₇₁to A₇₄ independently represents a nitrogen atom or C—R₇₁; R₇₁ representsa hydrogen atom or a substituent; each R₇₁ may be the same as ordifferent from every other R₇₁; m represents an integer of 1 or more;and L₇ represents a single bond or an m-valent linking group and islinked to any one of C atoms in Z₇₁, Z₇₂ and A₇₁ to A₇₄, provided thatwhen m is 1, then L₇ does not exist.

In the formula (7), though a combination of A₇₁ to A₇₄ is notparticularly limited, a number of the nitrogen atom in A₇₁ to A₇₄ ispreferably from 0 to 2, and more preferably from 0 to 1. m, L₇, Z₇₁ andZ₇₂ are respectively synonymous with m, L₅, Z₅₁ and Z₅₂ in the formula(5), and preferred ranges thereof are also the same.

R₇₁ is synonymous with R₂₂ in the formula (2), and a preferred rangethereof is also the same.

One of preferred embodiments as the compound represented by the formula(6) is concerned with a compound represented by the following formula(8).

In the formula (8), Z₈₂ represents an aromatic heterocyclic ring or anaromatic hydrocarbon ring; each of A₈₁ to A₈₇ independently represents anitrogen atom or C—R₈₁; R₈₁ represents a hydrogen atom or a substituent;each R₈₁ may be the same as or different from every other R₈₁; mrepresents an integer of 1 or more; and L₈ represents a single bond oran m-valent linking group and is linked to any one of C atoms in Z₈₂ andA₈₁ to A₈₇, provided that when m is 1, then L₈ does not exist.

In the formula (8), though a combination of A₈₁ to A₈₇ is notparticularly limited, a number of the nitrogen atom in A₈₁ to A₈₇ ispreferably from 0 to 4, and more preferably from 0 to 2. m, L₈, Z₈₂ andR₈₁ are respectively synonymous with m, L₆, Z₆₁ and R₆₁ in the formula(6), and preferred ranges thereof are also the same.

One of preferred embodiments as the compound represented by the formula(7) is concerned with a compound represented by the following formula(9).

In the formula (9), Z₉₁ represents an aromatic heterocyclic ring or anaromatic hydrocarbon ring; each of A₉₁ to A₉₈ independently represents anitrogen atom or C—R₉₁; R₉₁ represents a hydrogen atom or a substituent;each R₉₁ may be the same as or different from every other R₉₁; mrepresents an integer of 1 or more; and L₉ represents a single bond oran m-valent linking group and is linked to any one of C atoms in Z₉₁ andA₉₁ to A₉₈, provided that when m is 1, then L₉ does not exist.

In the formula (9), though a combination of A₉₁ to A₉₈ is notparticularly limited, a number of the nitrogen atom in A₉₁ to A₉₈ ispreferably from 0 to 4, and more preferably from 0 to 2. m, L₉, Z₉₁ andR₉₁ are respectively synonymous with m, L₇, Z₇₁ and R₇₁ in the formula(7), and preferred ranges thereof are also the same.

One of preferred embodiments as the compounds represented by theformulae (8) and (9) is concerned with a compound represented by thefollowing formula (10).

In the formula (10), each of A₁₀₁ to A₁₀₁₁ independently represents anitrogen atom or C—R₁₀₁; R₁₀₁ represents a hydrogen atom or asubstituent; each R₁₀₁ may be the same as or different from every otherR₁₀₁; m represents an integer of 1 or more; and L₁₀ represents a singlebond or an m-valent linking group and is linked to any one of C atoms inA₁₀₁ to A₁₀₁₁, provided that when m is 1, then L₁₀ does not exist.

In the formula (10), though a combination of A₁₀₁ to A₁₀₁₁ is notparticularly limited, a number of the nitrogen atom in A₁₀₁ to A₁₀₁₁ ispreferably from 0 to 6, and more preferably from 0 to 3. L₁₀, m and R₁₀₁are respectively synonymous with L₈, m and R₈₁ in the formula (8), andpreferred ranges thereof are also the same.

One of preferred embodiments as the compound represented by the formula(4) is concerned with a compound represented by the following formula(4-1).

The invention is also concerned with the compound represented by theformula (4-1). The compound represented by the formula (4-1) is a novelcompound and may be preferably used as a material for organicelectroluminescence devices.

In the formula (4-1), each of X₄₁₁ and X₄₁₂ independently representsC—R₄₁₁; R₄₁₁ represents a hydrogen atom or a substituent; each R₄₁₁ maybe the same as or different from every other R₄₁₁; each of A₄₁₁ to A₄₁₇independently represents a nitrogen atom or C—R₄₁₂; R₄₁₂ represents ahydrogen atom or a substituent; each R₄₁₂ may be the same as ordifferent from every other R₄₁₂; L₄₁ represents a single bond or anm-valent linking group and is linked to any one of C atoms in X₄₁₁, X₄₁₂and A₄₁₁ to A₄₁₇; when the linking group is an aromatic hydrocarbon ringgroup or an aromatic heterocyclic group, then a size of the ring is froma 5-membered to 6-membered ring; and m represents an integer of 2 ormore.

In the formula (4-1), X₄₁₁, X₄₁₂, A₄₁₁ to A₄₁₇, L₄₁, R₄₁₁ and R₄₁₂ arerespectively synonymous with X₄₁, X₄₂, A₄₁ to A₄₇, L₄, R₄₁ and R₄₂ inthe formula (4), and preferred ranges thereof are also the same.

One of preferred embodiments as the compound represented by the formula(4-1) is concerned with a compound represented by the following formula(4-2).

The formula (4-2) is described. Each of X₄₂₁ and X₄₂₂ independentlyrepresents C—R₄₂₁; R₄₂₁ represents a hydrogen atom or a substituent;each R₄₂₁ may be the same as or different from every other R₄₂₁; each ofA₄₂₁ to A₄₂₇ independently represents a nitrogen atom or C—R₄₂₂; R₄₂₂represents a hydrogen atom or a substituent; each R₄₂₂ may be the sameas or different from every other R₄₂₂; R₄₂₃ represents a hydrogen atomor a substituent; each R₄₂₃ may be the same as or different from everyother R₄₂₃; m represents an integer of from 2 to 4; and a siliconlinking group is linked to any one of C atoms in X₄₂₁, X₄₂₂ and A₄₂₁ toA₄₂₇.

In the formula (4-2), X₄₂₁, X₄₂₂, A₄₂₁ to A₄₂₇, R₄₂₁ and R₄₂₂ arerespectively synonymous with X₄₁₁, X₄₁₂, A₄₁₁ to A₄₁₇, R₄₁₁ and R₄₁₂ inthe formula (4-1), and preferred ranges thereof are also the same.

R₄₂₃ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group or a silyloxy group; more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group or an aromatic heterocyclic group; further more preferablyan alkyl group, an aromatic hydrocarbon ring group, a cyano group or anaromatic heterocyclic group; especially preferably an alkyl group, anaromatic hydrocarbon ring group or an aromatic heterocyclic group; andmost preferably an alkyl group or a phenyl group. Each R₄₂₃ may be thesame as or different from every other R₄₂₃.

One of preferred embodiments as the compound represented by the formula(4-1) is concerned with a compound represented by the following formula(4-3).

The formula (4-3) is described. Each of X₄₃₁ and X₄₃₂ independentlyrepresents C—R₄₃₁; R₄₃₁ represents a hydrogen atom or a substituent;each R₄₃₁ may be the same as or different from every other R₄₃₁; each ofA₄₃₁ to A₄₃₇ independently represents a nitrogen atom or C—R₄₃₂; R₄₃₂represents a hydrogen atom or a substituent; each R₄₃₂ may be the sameas or different from every other R₄₃₂; R₄₃₃ represents a hydrogen atomor a substituent; each R₄₃₃ may be the same as or different from everyother R₄₃₃; m represents an integer of from 2 to 4; and a carbon linkinggroup is linked to any one of C atoms in X₄₃₁, X₄₃₂ and A₄₃₁ to A₄₃₇.

In the formula (4-3), X₄₃₁, X₄₃₂, A₄₃₁ to A₄₃₇, R₄₃₁ and R₄₃₂ arerespectively synonymous with X₄₁₁, X₄₁₂, A₄₁₁ to A₄₁₇, R₄₁₁ and R₄₁₂ inthe formula (4-1), and preferred ranges thereof are also the same.

R₄₃₃ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group or a silyloxy group; more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group or an aromatic heterocyclic group; further more preferablyan alkyl group, an aromatic hydrocarbon ring group, a cyano group or anaromatic heterocyclic group; especially preferably an alkyl group, anaromatic hydrocarbon ring group or an aromatic heterocyclic group; andmost preferably an alkyl group or a phenyl group. Of these, a methylgroup is preferable. Each R₄₃₃ may be the same as or different fromevery other R₄₃₃.

One of preferred embodiments as the compound represented by the formula(4-1) is concerned with a compound represented by the following formula(4-4).

The formula (4-4) is described. Each of X₄₄₁ and X₄₄₂ independentlyrepresents C—R₄₄₁; R₄₄₁ represents a hydrogen atom or a substituent;each R₄₄₁ may be the same as or different from every other R₄₄₁; each ofA₄₄₁ to A₄₄₇ independently represents a nitrogen atom or C—R₄₄₂; R₄₄₂represents a hydrogen atom or a substituent; each R₄₄₂ may be the sameas or different from every other R₄₄₂; Ar₄₄ represents an aromatichydrocarbon ring or aromatic heterocyclic ring, and a size of the ringis from 5-membered to 6-membered ring; Ar₄₄ is linked to any one of Catoms in X₄₄₁, X₄₄₂ and A₄₄₁ to A₄₄₇; R₄₄₃ represents a hydrogen atom ora substituent; each R₄₄₃ may be the same as or different from everyother R₄₄₃; m represents an integer of 2 or more; and n represents aninteger of 0 or more.

In the formula (4-4), X₄₄₁, X₄₄₂, A₄₄₁ to A₄₄₇, R₄₄₁ and R₄₄₂ arerespectively synonymous with X₄₁₁, X₄₁₂, A₄₁₁ to A₄₁₇, R₄₁₁ and R₄₁₂ inthe formula (4-1), and preferred ranges thereof are also the same.

R₄₄₃ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group or a silyloxy group; more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group or an aromatic heterocyclic group; further more preferablyan alkyl group, an aromatic hydrocarbon ring group, a cyano group or anaromatic heterocyclic group; and especially preferably an alkyl group,an aromatic hydrocarbon ring group or an aromatic heterocyclic group.Each R₄₄₃ may be the same as or different from every other R₄₄₃.

Ar₄₄ represents a 5-membered to 6-membered aromatic hydrocarbon ring oraromatic heterocyclic ring. The 5-membered to 6-membered aromatichydrocarbon ring or aromatic heterocyclic ring represented by Ar₄₄ ispreferably a 6-membered ring.

Though the aromatic heterocyclic ring represented by Ar₄₄ is notparticularly limited with respect to the hetero atom to be containedtherein, it is preferably an aromatic heterocyclic ring containingnitrogen, oxygen, sulfur, selenium, silicon, germanium or phosphorus;more preferably an aromatic heterocyclic ring containing nitrogen,oxygen or sulfur; further more preferably an aromatic heterocyclic ringcontaining nitrogen or oxygen; and especially preferably an aromaticheterocyclic ring containing nitrogen. Though a number of the heteroatom which is contained in one aromatic heterocyclic ring represented byAr₄₄ is not particularly limited, it is preferably from 1 to 3.

Specific examples of the 5-membered to 6-membered aromatic hydrocarbonring or aromatic heterocyclic ring represented by Ar₄₄ include a benzenering, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazinering, a pyridazine ring, a pyrrole ring, a pyrazole ring, an imidazolering, a triazole ring, an oxazole ring, an oxadiazole ring, a thiazolering, a thiadiazole ring, a furan ring, a thiophene ring, a selenophenering, a silole ring, a germole ring and a phosphole ring.

The aromatic hydrocarbon ring or aromatic heterocyclic ring formed fromAr₄₄ may have a substituent. As the substituent, those which areexemplified previously as the group A of substituent are applicable.

The 5-membered to 6-membered aromatic hydrocarbon ring or aromaticheterocyclic ring represented by Ar₄₄ is preferably a benzene ring, apyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, apyrrole ring, a pyrazole ring, an imidazole ring, a triazole ring, anoxazole ring, a thiazole ring, a furan ring or a thiophene ring; morepreferably a benzene ring, a pyridine ring, a pyrazine ring, a pyrrolering, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazolering or a thiophene ring; further more preferably a benzene ring, apyridine ring, a pyrazine ring, a pyrazole ring, an imidazole ring or athiophene ring; and especially preferably a benzene ring, a pyridinering or a pyrazine ring.

m represents an integer of 2 or more, preferably from 2 to 6, and morepreferably from 2 to 4. n represents an integer of 0 or more, preferablyfrom 0 to 4, and more preferably from 2 to 4.

One of preferred embodiments as the compound represented by the formula(4-1) is concerned with a compound represented by the following formula(4-5).

In the formula (4-5), each of X₄₅₁ and X₄₅₂ independently representsC—R₄₅₁; R₄₅₁ represents a hydrogen atom or a substituent; each R₄₅₁ maybe the same as or different from every other R₄₅₁; each of A₄₅₁ to A₄₅₇independently represents a nitrogen atom or C—R₄₅₂; R₄₅₂ represents ahydrogen atom or a substituent; each R₄₅₂ may be the same as ordifferent from every other R₄₅₂; R₄₅₃ represents a hydrogen atom or asubstituent; each R₄₅₃ may be the same as or different from every otherR₄₅₃; n represents an integer of 1 or more; and a silicon substituent islinked to any one of C atoms in X₄₅₁, X₄₅₂ and A₄₅₁ to A₄₅₇.

In the formula (4-5), X₄₅₁, X₄₅₂, A₄₅₁ to A₄₅₇, R₄₅₁ and R₄₅₂ arerespectively synonymous with X₄₁₁, X₄₁₂, A₄₁₁ to A₄₁₇, R₄₁₁ and R₄₁₂ inthe formula (4-1), and preferred ranges thereof are also the same.

R₄₅₃ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group or a silyloxy group; more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group or an aromatic heterocyclic group; further more preferablyan alkyl group, an aromatic hydrocarbon ring group, a cyano group or anaromatic heterocyclic group; especially preferably an alkyl group, anaromatic hydrocarbon ring group or an aromatic heterocyclic group;especially preferably an alkyl group or a phenyl group; and mostpreferably a phenyl group.

n represents an integer of 0 or more, preferably from 0 to 4, and morepreferably from 0 to 2.

One of preferred embodiments as the compound represented by the formula(4-1) is concerned with a compound represented by the following formula(10-1).

The formula (10-1) is described. Each of A₁₀₁₁ to A₁₀₁₁₁ independentlyrepresents a nitrogen atom or C—R₁₀₁₁; R₁₀₁₁ represents a hydrogen atomor a substituent; each R₁₀₁₁ may be the same as or different from everyother R₁₀₁₁; L₁₀₁ represents a single bond or an m-valent linking groupand is linked to any one of C atoms in A₁₀₁₁ to A₁₀₁₁₁; when the linkinggroup is an aromatic hydrocarbon ring group or an aromatic heterocyclicgroup, then a size of the ring is from a 5-membered to 6-membered ring;and m represents an integer of 2 or more.

In the formula (10-1), A₁₀₁₁ to A₁₀₁₁₁, L₁₀₁ and R₁₀₁₁ are respectivelysynonymous with A₁₀₁ to A₁₀₁₁, L₁₀ and R₁₀₁ in the formula (10), andpreferred ranges thereof are also the same.

m represents an integer of 2 or more, preferably from 2 to 6, morepreferably from 2 to 4, further more preferably 2 or 3, and especiallypreferably 2.

One of preferred embodiments as the compound represented by the formula(10-1) is concerned with a compound represented by the following formula(10-2).

The formula (10-2) is described. Each of A₁₀₂₁ to A₁₀₂₁₁ independentlyrepresents a nitrogen atom or C—R₁₀₂₁; R₁₀₂₁ represents a hydrogen atomor a substituent; each R₁₀₂₁ may be the same as or different from everyother R₁₀₂₁; R₁₀₂₂ represents a hydrogen atom or a substituent; eachR₁₀₂₂ may be the same as or different from every other R₁₀₂₂; mrepresents an integer of from 2 to 4; and a silicon linking group islinked to any one of C atoms in A₁₀₂₁ to A₁₀₂₁₁.

In the formula (10-2), A₁₀₂₁ to A₁₀₂₁₁ and R₁₀₂₁ are respectivelysynonymous with A₁₀₁₁ to A₁₀₁₁₁ and R₁₀₁₁ in the formula (10-1), andpreferred ranges thereof are also the same.

R₁₀₂₂ is synonymous with R₄₂₃ in the formula (4-2), and a preferredrange thereof is also the same.

One of preferred embodiments as the compound represented by the formula(10-1) is concerned with a compound represented by the following formula(10-3).

The formula (10-3) is described. Each of A₁₀₃₁ to A₁₀₃₁₁ independentlyrepresents a nitrogen atom or C—R₁₀₃₁; R₁₀₃₁ represents a hydrogen atomor a substituent; each R₁₀₃₁ may be the same as or different from everyother R₁₀₃₁; R₁₀₃₂ represents a hydrogen atom or a substituent; eachR₁₀₃₂ may be the same as or different from every other R₁₀₃₂; mrepresents an integer of from 2 to 4; and a carbon linking group islinked to any one of C atoms in A₁₀₃₁ to A₁₀₃₁₁.

In the formula (10-3), A₁₀₃₁ to A₁₀₃₁₁ and R₁₀₃₁ are respectivelysynonymous with A₁₀₁₁ to A₁₀₁₁₁ and R₁₀₁₁ in the formula (10-1), andpreferred ranges thereof are also the same.

R₁₀₃₂ is synonymous with R₄₃₃ in the formula (4-3), and a preferredrange thereof is also the same.

One of preferred embodiments as the compound represented by the formula(10-1) is concerned with a compound represented by the following formula(10-4).

The formula (10-4) is described. Each of A₁₀₄₁ to A₁₀₄₁₁ independentlyrepresents a nitrogen atom or C—R₁₀₄₁; R₁₀₄₁ represents a hydrogen atomor a substituent; each R₁₀₄₁ may be the same as or different from everyother R₁₀₄₁; Ar₁₀₄ represents an aromatic hydrocarbon ring or aromaticheterocyclic ring, and a size of the ring is from 5-membered to6-membered ring; Ar₁₀₄ is linked to any one of C atoms in A₁₀₄₁ toA₁₀₄₁₁; R₁₀₄₂ represents a hydrogen atom or a substituent; each R₁₀₄₂may be the same as or different from every other R₁₀₄₂; m represents aninteger of 2 or more; and n represents an integer of 0 or more.

In the formula (10-4), A₁₀₄₁ to A₁₀₄₁₁ and R₁₀₄₁ are respectivelysynonymous with A₁₀₁₁ to A₁₀₁₁₁ and R₁₀₁₁ in the formula (10-1), andpreferred ranges thereof are also the same.

R₁₀₄₂ is synonymous with R₄₄₃ in the formula (4-4), and a preferredrange thereof is also the same.

Ar₁₀₄ represents a 5-membered to 6-membered aromatic hydrocarbon ring oraromatic heterocyclic ring. The 5-membered to 6-membered aromatichydrocarbon ring or aromatic heterocyclic ring represented by Ar₁₀₄ ispreferably a 6-membered ring.

Though the aromatic heterocyclic ring represented by Ar₁₀₄ is notparticularly limited with respect to the hetero atom to be containedtherein, it is preferably an aromatic heterocyclic ring containingnitrogen, oxygen, sulfur, selenium, silicon, germanium or phosphorus;more preferably an aromatic heterocyclic ring containing nitrogen,oxygen or sulfur; further more preferably an aromatic heterocyclic ringcontaining nitrogen or oxygen; and especially preferably an aromaticheterocyclic ring containing nitrogen. Though a number of the heteroatom which is contained in one aromatic heterocyclic ring represented byAr₁₀₄ is not particularly limited, it is preferably from 1 to 3.

Specific examples of the 5-membered to 6-membered aromatic hydrocarbonring or aromatic heterocyclic ring represented by Ar₁₀₄ include abenzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, atriazine ring, a pyridazine ring, a pyrrole ring, a pyrazole ring, animidazole ring, a triazole ring, an oxazole ring, an oxadiazole ring, athiazole ring, a thiadiazole ring, a furan ring, a thiophene ring, aselenophene ring, a silole ring, a germole ring and a phosphole ring.

The aromatic hydrocarbon ring or aromatic heterocyclic ring formed fromAr₁₀₄ may have a substituent. As the substituent, those which areexemplified previously as the group A of substituent are applicable.

The 5-membered to 6-membered aromatic hydrocarbon ring or aromaticheterocyclic ring represented by Ar₁₀₄ is preferably a benzene ring, apyridine ring, a pyrazine ring, a pyrimidine ring, a triazine ring, apyrrole ring, a pyrazole ring, an imidazole ring, a triazole ring, anoxazole ring, a thiazole ring, a furan ring or a thiophene ring; morepreferably a benzene ring, a pyridine ring, a pyrazine ring, a pyrrolering, a pyrazole ring, an imidazole ring, an oxazole ring, a thiazolering or a thiophene ring; further more preferably a benzene ring, apyridine ring, a pyrazine ring, a pyrazole ring, an imidazole ring or athiophene ring; and especially preferably a benzene ring, a pyridinering or a pyrazine ring.

m represents an integer of 2 or more, preferably from 2 to 6, and morepreferably from 2 to 4. n represents an integer of 0 or more, preferablyfrom 0 to 4, and more preferably from 2 to 4.

One of preferred embodiments as the compound represented by the formula(10-1) is concerned with a compound represented by the following formula(10-5).

In the formula (10-5), each of A₁₀₅₁ to A₁₀₅₁₁ independently representsa nitrogen atom or C—R₁₀₅₁; R₁₀₅₁ represents a hydrogen atom or asubstituent; each R₁₀₅₁ may be the same as or different from every otherR₁₀₅₁; R₁₀₅₂ represents a hydrogen atom or a substituent; each R₁₀₅₂ maybe the same as or different from every other R₁₀₅₂; n represents aninteger of 1 or more; and a silicon linking group is linked to any oneof C atoms in A₁₀₅₁ to A₁₀₅₁₁.

R₁₀₅₂ is preferably a hydrogen atom, an alkyl group, an aromatichydrocarbon ring group, an amino group, an alkoxy group, an aryloxygroup, an aromatic heterocyclic oxy group, an alkylthio group, anarylthio group, a heterocyclic thio group, a cyano group, an aromaticheterocyclic group, a silyl group or a silyloxy group; more preferablyan alkyl group, an aromatic hydrocarbon ring group, an amino group, acyano group or an aromatic heterocyclic group; further more preferablyan alkyl group, an aromatic hydrocarbon ring group, a cyano group or anaromatic heterocyclic group; especially preferably an alkyl group, anaromatic hydrocarbon ring group or an aromatic heterocyclic group;especially preferably an alkyl group or a phenyl group; and mostpreferably a phenyl group.

n represents an integer of 0 or more, preferably from 0 to 4, and morepreferably from 0 to 2.

In the invention, the compound represented by the formula (1) of theinvention is not limited with respect to its applications and may becontained in any layer within the organic layer. As to the layer intowhich the compound represented by the formula (1) of the invention isintroduced, the compound represented by the formula (1) of the inventionis preferably contained in any one or a plurality of a light emittinglayer, a hole injection layer, a hole transport layer, an electrontransport layer, an electron injection layer, an exciton blocking layerand a charge blocking layer.

From the viewpoint of bearing the injection transport of a hole, thecompound represented by the formula (1) of the invention is preferablycontained in a light emitting layer, a hole injection layer or a holetransport layer.

From the viewpoint of stability of a material against the excitationstate which is generated through recombination of an electron and ahole, it is especially preferable that the compound represented by anyone of the formulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5) iscontained in the light emitting layer.

In the light emitting layer, the compound represented by the formula (1)of the invention is contained in an amount of preferably from 10 to 99%by mass, more preferably from 40 to 99% by mass, and further morepreferably from 60 to 99% by mass (In this specification, mass ratio isequal to weight ratio).

In the invention, the compound represented by the formula (1) ispreferably contained in any one of the light emitting layer or a layeradjacent to the light emitting layer. In the case where the compoundrepresented by the formula (1) is contained in a layer adjacent to thelight emitting layer, it is preferable from the standpoint of uniformityof the film that the layer is constituted of the compound represented bythe formula (1) singly.

It is preferable that a hole transport layer is provided between thelight emitting layer and an anode and that the compound represented byany one of the formulae (1) to (10), (4-1) to (4-5) and (10-1) to (10-5)is contained in the hole transport layer.

Also, it is preferable that an electron transport layer is providedbetween the light emitting layer and a cathode and that the compoundrepresented by any one of the formulae (1) to (10), (4-1) to (4-5) and(10-1) to (10-5) is contained in the electron transport layer. Accordingto this, it is possible to efficiently inject an electron from thecathode.

The compound represented by the formula (1) may be contained in both ofthe light emitting layer and the adjacent layer thereto.

Also, in the case where the compound represented by the formula (1) ofthe invention is contained in the hole transport layer, the compoundrepresented by the formula (1) of the invention is contained in anamount of preferably from 50 to 100% by mass, more preferably from 70 to100% by mass, and further more preferably 100% by mass.

In the case where the compound represented by the formula (1) of theinvention is contained the electron transport layer, the compoundrepresented by the formula (1) of the invention is contained in anamount of preferably from 50 to 100% by mass, more preferably from 70 to100% by mass, and further more preferably 100% by mass.

A degree of charge transfer of a host material which is contained in thelight emitting layer is preferably 1×10⁻⁶ cm²/Vs or more and not morethan 1×10⁻¹ cm²/Vs, more preferably 5×10⁻⁶ cm²/Vs or more and not morethan 1×10⁻² cm²/Vs, further more preferably 1×10⁻⁵ cm²/Vs or more andnot more than 1×10⁻² cm²/Vs, and especially preferably 5×10⁻⁵ cm²/Vs ormore and not more than 1×10⁻² cm²/Vs.

A T₁ level (minimum excitation triplet energy level) of the compoundrepresented by the formula (1) which is contained in the luminescencedevice of the invention is preferably 60 kcal/mole or more (251.4kJ/mole or more) and not more than 95 kcal/mole (not more than 398.1kJ/mole), more preferably 62 kcal/mole or more (259.78 kJ/mole or more)and not more than 85 kcal/mole (not more than 356.15 kJ/mole), andfurther more preferably 65 kcal/mole or more (272.35 kJ/mole or more)and not more than 80 kcal/mole (not more than 335.2 kJ/mole). What theminimum excitation triplet energy level falls within the foregoing rangeis preferable because a device with a short emission wavelength (forexample, a blue device) may be efficiently emitted.

A T₁ level (minimum excitation triplet energy level) of the layeradjacent to the light emitting layer of the luminescence device of theinvention is preferably 60 kcal/mole or more (251.4 kJ/mole or more) andnot more than 95 kcal/mole (not more than 398.1 kJ/mole), morepreferably 62 kcal/mole or more (259.78 kJ/mole or more) and not morethan 85 kcal/mole (not more than 356.15 kJ/mole), and further morepreferably 65 kcal/mole or more (272.35 kJ/mole or more) and not morethan 80 kcal/mole (not more than 335.2 kJ/mole).

Next, examples of the compounds represented by the formulae (1) to (10),(4-1) to (4-5) and (10-1) to (10-5) which are used in the organicelectroluminescence device of the invention are given below, but itshould not be construed that the invention is limited thereto.

Compound Central skeleton A 46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

67

68

69

70

Compound Central skeleton A 110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

The compounds represented by the formulae (1) to (10) may be synthesizedby various known synthesis methods described in, for example, J. Chem.Soc., pages 1945 to 1956 (1939), J. Chem. Soc., pages 2750 to 2755(1958), etc. The compounds represented by the formulae (4-1) to (4-5)and (10-1) to (10-5) may be synthesized using the foregoing intermediateD by various known synthesis methods described in, for example, J. Org.Chem., 20, pages 73 to 78 (1955), Org. Lett., 7, pages 2829 to 2832(2005), J. Am. Chem. Soc., 128, pages 8549 to 8558 (2006), Chem. Lett.,36, pages 1156 to 1157 (2007), etc.

A glass transition temperature of the compound represented by theformula (1) is preferably 130° C. or higher and not higher than 450° C.,more preferably 140° C. or higher and not higher than 450° C., andfurther more preferably 160° C. or higher and not higher than 450° C.What the glass transition temperature of the compound represented by theformula (1) falls within the foregoing range is preferable because heatresistance and durability of the device may be expected to be enhanced.

[Organic Electroluminescence Device]

The device of the invention includes a cathode and an anode on asubstrate and includes an organic layer containing a light emittinglayer between the both electrodes. In view of natures of theluminescence device, it is preferable that at least one electrode of theanode and the cathode is transparent.

In the invention, as to a form of lamination of the organic layers, anembodiment in which a hole transport layer, a light emitting layer andan electron transport layer are laminated in this order from the anodeside is preferable. Furthermore, a hole injection layer is providedbetween the hole transport layer and the anode, and/or an electrontransporting interlayer is provided between the light emitting layer andthe electron transport layer. Also, a hole transporting interlayer maybe provided between the light emitting layer and the hole transportlayer, and an electron injection layer may be similarly provided betweenthe cathode and the electron transport layer.

Each of the layers may be divided into plural secondary layers.

Each of the layers configuring the organic layer may be suitablyfabricated by any method, for example, a dry fabrication process such asa vapor deposition process and a sputtering process, a transfer process,a printing process, a coating process, an inkjet process, a sprayingprocess, etc.

Next, each of the elements configuring the organic EL device of theinvention is described.

<Substrate>

It is preferable that the substrate is a substrate which does notscatter or decay light emitted from the organic compound layer. Specificexamples thereof include inorganic materials such as yttria-stabilizedzirconia (YSZ) and a glass; and organic materials such as polyesters(for example, polyethylene terephthalate, polybutylene phthalate,polyethylene naphthalate, etc.), polystyrenes, polycarbonates,polyethersulfones, polyarylates, polyimides, polycycloolefins,norbornene resins and poly(chlorotrifluoroethylene).

For example, in the case where a glass is used as the substrate, withrespect to the material quality thereof, for the purpose of reducing theamount of eluted ions from the glass, it is preferred to use a no-alkaliglass. Also, in the case of using a soda lime glass, it is preferred touse a glass to which barrier coating with silica, etc. has been applied.In the case of an organic material, it is preferable that the organicmaterial is excellent in heat resistance, dimensional stability, solventresistance, electrical insulating properties and processability.

The substrate is not particularly limited with respect to its shape,structure and size and so on and may be properly chosen depending uponthe application and purpose and the like of the organic EL device. Ingeneral, the shape of the substrate is preferably a platy shape. Thestructure of the substrate may be a single layer structure or may be alaminate structure. Also, the substrate may be formed of a singlecomponent or may be formed of two or more components.

Though the substrate may be colorless transparent or may be coloredtransparent, it is preferably colorless transparent from the standpointthat it does not scatter or decay light emitted from the light emittinglayer.

The substrate may be provided with a moisture permeation preventinglayer (gas barrier layer) on the front or back surface thereof.

As a material of the moisture permeation preventing layer (gas barrierlayer), an inorganic material such as silicon nitride and silicon oxideis suitably used. The moisture permeation preventing layer (gas barrierlayer) may be fabricated by, for example, a high-frequency sputteringprocess, etc.

In the case of using a thermoplastic substrate, a hard coat layer, anundercoat layer or the like may be further provided as the need arises.

<Anode>

In general, the anode may have a function as an electrode for feeding ahole into the organic compound layer. The anode is not particularlylimited with respect to its shape, structure and size and so on and maybe properly chosen among known electrode materials depending upon theapplication and purpose of the organic EL device. As describedpreviously, the anode is usually provided as a transparent anode.

Suitable examples of a material of the anode include metals, alloys,metal oxides, conductive compounds and mixtures thereof. Specificexamples of the anode material include conductive metal oxides such astin oxide doped with antimony, fluorine, etc. (for example, ATO, FTO,etc.), tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO) andindium zinc oxide (IZO); metals such as gold, silver, chromium andnickel; mixtures or laminates of the foregoing metal and conductivemetal oxide; inorganic conductive substances such as copper iodide andcopper sulfide; organic conductive materials such as polyaniline,polythiophene and polypyrrole; and laminates thereof with ITO. Of these,conductive metal oxides are preferable; and ITO is especially preferablefrom the standpoints of productivity, high conductivity, transparencyand so on.

The anode may be fabricated on the foregoing substrate according to amethod properly chosen while taking into consideration the adaptabilityto the material constituting the anode among, for example, a wet system(for example, a printing system, a coating system, etc.), a physicalsystem (for example, a vacuum vapor deposition process, a sputteringprocess, an ion plating process, etc.), a chemical system (for example,a CVD process, a plasma CVD process, etc.) and so on. For example, inthe case where ITO is chosen as the material of the anode, thefabrication of the anode can be carried out according to a directcurrent or high-frequency sputtering process, a vacuum vapor depositionprocess, an ion plating process, etc.

In the organic EL device of the invention, though the fabricationposition of the anode is not particularly limited and may be properlychosen depending upon the application and purpose of the organic ELdevice, it is preferable that the anode is fabricated on the substrate.In that case, the anode may be fabricated on the whole or a part of onesurface of the substrate.

Patterning in fabricating the anode may be carried out by means ofchemical etching such as photolithography or may be carried out by meansof physical etching with a laser, etc. Also, patterning may be carriedout by superimposing a mask and undergoing vacuum vapor deposition orsputtering or the like or may be carried out by a liftoff process or aprinting process.

A thickness of the anode may be properly chosen depending upon thematerial constituting the anode and cannot be unequivocally defined. Thethickness of the anode is usually from about 10 nm to 50 μm, andpreferably from 50 nm to 20 μm.

A resistivity value of the anode is preferably not more than 10³Ω/□. Inthe case where the anode is transparent, the anode may be colorlesstransparent or may be colored transparent. In order to collect lightemission from the transparent anode side, its transmittance ispreferably 60% or more, and more preferably 70% or more.

The transparent anode is described in detail in New Developments ofTransparent Conductive Films, supervised by Yutaka Sawada (published byCMC Publishing Co., Ltd., 1999), and the matters described therein areapplicable to the invention. In the case of using a plastic basematerial with low heat resistance, a transparent anode obtained by usingITO or IZO and fabricating it at a low temperature of not higher than150° C. is preferable.

<Cathode>

In general, the cathode may have a function as an electrode forinjecting an electron into the organic compound layer. The cathode isnot particularly limited with respect to its shape, structure and sizeand so on and may be properly chosen among known electrode materialsdepending upon the application and purpose of the organic EL device.

Examples of a material constituting the cathode include metals, alloys,metal oxides, electrically conductive compounds and mixtures thereof.Specific examples of the cathode material include alkali metals (forexample, Li, Na, K, Cs, etc.), alkaline earth metals (for example, Mg,Ca, etc.), gold, silver, lead, aluminum, a sodium-potassium alloy, alithium-aluminum alloy, a magnesium-silver alloy, indium and rare earthmetals (for example, ytterbium, etc.). Though such a material may beused singly, two or more kinds thereof may be suitably used jointly fromthe viewpoint of making both stability and electron injection propertiescompatible with each other.

Of these, alkali metals and alkaline earth metals are preferable as thematerial constituting the cathode from the standpoint of electroninjection properties; and materials composed mainly of aluminum arepreferable from the standpoint of excellent storage stability.

The material composed mainly of aluminum as referred to herein refers toa single substance of aluminum or an alloy of aluminum and from 0.01 to10% by mass of an alkali metal or an alkaline earth metal or a mixturethereof (for example, a lithium-aluminum alloy, a magnesium-aluminumalloy, etc.).

The material of the cathode is disclosed in detail in JP-A-2-15595 andJP-A-5-121172, and materials disclosed in these patent documents arealso applicable in the invention.

The method for fabricating the cathode is not particularly limited, andthe fabrication of the cathode may be carried out according to a knownmethod. The cathode may be fabricated according to a method properlychosen while taking into consideration the adaptability to the materialconstituting the cathode among, for example, a wet system (for example,a printing system, a coating system, etc.), a physical system (forexample, a vacuum vapor deposition process, a sputtering process, an ionplating process, etc.), a chemical system (for example, a CVD process, aplasma CVD process, etc.) and so on. For example, in the case where ametal or the like is chosen as the material of the cathode, the cathodemay be fabricated by a simultaneous or sequential sputtering process ofone or two or more kinds thereof or the like.

Patterning in fabricating the cathode may be carried out by means ofchemical etching such as photolithography or may be carried out by meansof physical etching with a laser, etc. Also, patterning may be carriedout by superimposing a mask and undergoing vacuum vapor deposition orsputtering or the like or may be carried out by a liftoff process or aprinting process.

The fabrication position of the cathode is not particularly limited. Thecathode may be fabricated on the whole or a part of the organic layer.

Also, a dielectric layer made of a fluoride or oxide of an alkali metalor an alkaline earth metal, etc. may be inserted in a thickness of from0.1 to 5 nm between the cathode and the organic compound layer. Thisdielectric layer may also be considered as a sort of the electroninjection layer. The dielectric layer may be fabricated by, for example,a vacuum vapor deposition process, a sputtering process, an ion platingprocess or the like.

A thickness of the cathode may be properly chosen depending upon thematerial constituting the cathode and cannot be unequivocally defined.The thickness of the cathode is usually from about 10 nm to 5 μm, andpreferably from 50 nm to 1 μm.

Also, the cathode may be transparent or may be opaque. A transparentcathode may be fabricated by thinly fabricating the material of thecathode in a thickness of from 1 to 10 nm and further laminating atransparent conductive material such as ITO and IZO.

<Organic Layer>

The organic layer in the invention is described.

The organic EL device of the invention has at least one organic layerincluding the light emitting layer. As described previously, examples ofother organic layers than the light emitting layer include respectivelayers such as a hole transport layer, an electron transport layer, acharge blocking layer, a hole injection layer and an electron injectionlayer.

In the organic EL device of the invention, the respective layersconfiguring the organic layer may be suitably fabricated by any of a dryfabrication process (for example, a vapor deposition process, asputtering process, etc.), a wet coating system, a transfer process, aprinting process, an inkjet system and so on.

—Light Emitting Layer—

The light emitting layer is a layer having functions such that at thetime of impressing an electric field, it receives a hole from the anode,the hole injection layer or the hole transport layer, receives anelectron from the cathode, the electron injection layer or the electrontransport layer and provides a site of recombination of the hole and theelectron, thereby achieving light emission.

Also, the light emitting layer may be configured of only a lightemitting material or may be configured as a mixed layer of a hostmaterial and a light emitting material.

Also, the light emitting layer may be made of a single layer or two ormore layers. The respective layers may emit light in a differentluminescent color from each other.

<Light Emitting Material>

Though the light emitting material may be a fluorescent material or aphosphorescent material, it is more preferably a phosphorescentmaterial. A dopant may be made of a single kind or two or more kinds.

It is preferable that the light emitting layer contains a phosphorescentmaterial.

It is preferable that the host material is a charge transport material.The host material may be made of a single kind or two or more kinds.Examples thereof include a configuration in which an electrontransporting host material and a hole transporting host material aremixed. Furthermore, the light emitting layer may contain a materialwhich does not have charge transporting properties and which does notemit light.

<<Fluorescent Material>>

In general, examples of the fluorescent material include benzoxazole,benzimidazole, benzothiazole, styrylbenzene, polyphenyl,diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran,perinone, oxadiazole, aldazine, pyralizine, cyclopentadiene,bisstyrylanthracene, quinacridone, pyrolopyridine, thiadiazolopyridine,cyclopentadiene, styrylamine, aromatic dimethylidine compounds,condensed polycyclic aromatic compounds (for example, anthracene,phenanthroline, pyrene, perylene, rubrene, pentacence, etc.), variousmetal complexes (represented by metal complexes of 8-quinolinol,pyrromethene complexes and rare earth complexes), polymer compounds (forexample, polythiophene, polyphenylene, polyphenylene vinylene), organicsilanes and derivatives thereof.

<<Phosphorescent Material>>

In general, examples of the phosphorescent material include complexescontaining a transition metal atom or a lanthanoid atom.

Though the transition metal atom is not particularly limited, preferredexamples thereof include ruthenium, rhodium, palladium, tungsten,rhenium, osmium, iridium, gold, silver, copper and platinum. Of these,rhenium, iridium and platinum are more preferable; and iridium andplatinum are further more preferable.

Examples of the lanthanoid atom include lanthanum, cerium, praseodymium,neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium,erbium, thulium, ytterbium and lutetium. Of these lanthanoid atoms,neodymium, europium and gadolinium are preferable.

Examples of a ligand of the complex include ligands described in, forexample, G. Wilkinson, et al., Comprehensive Coordination Chemistry,published by Pergamon Press, 1987; H. Yersin, Photochemistry andPhotophysics of Coordination Compounds, published by Springer-Verlag,1987; and YAMAMOTO, Akio, Organometallic Chemistry—Principles andApplications, published by Shokabo Publishing Co., Ltd., 1982.

Specifically, as the ligand, halogen ligands (preferably a chlorineligand), aromatic carbocyclic ligands (preferably aromatic carbocyclicligands having from 5 to 30 carbon atoms, more preferably from 6 to 30carbon atoms, further more preferably from 6 to 20 carbon atoms, andespecially preferably from 6 to 12 carbon atoms; for example, acyclopentadienyl anion, a benzene anion, a naphthyl anion, etc.),nitrogen-containing heterocyclic ligands (preferably nitrogen-containingheterocyclic ligands having from 5 to 30 carbon atoms, more preferablyfrom 6 to 30 carbon atoms, further more preferably from 6 to 20 carbonatoms, and especially preferably from 6 to 12 carbon atoms; for example,phenylpyridine, benzoquinoline, quinolinol, bipyridyl, phenanthroline,etc.), diketone ligands (for example, acetylacetone, etc.), carboxylicacid ligands (preferably carboxylic acid ligands having from 2 to 30carbon atoms, more preferably from 2 to 20 carbon atoms, and furthermore preferably from 2 to 16 carbon atoms; for example, an acetic acidligand, etc.), alcoholate ligands (preferably alcoholate ligands havingfrom 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms,and further more preferably from 6 to 20 carbon atoms; for example, aphenolate ligand, etc.), silyloxy ligands (preferably silyloxy ligandshaving from 3 to 40 carbon atoms, more preferably from 3 to 30 carbonatoms, and further more preferably from 3 to 20 carbon atoms; forexample, a trimethylsilyloxy ligand, a dimethyl-tert-butylsilyloxyligand, a triphenylsilyloxy ligand, etc.), a carbon monoxide ligand, anisonitrile ligand, a cyano ligand, phosphorus ligands (preferablyphosphorus ligands having from 3 to 40 carbon atoms, more preferablyfrom 3 to 30 carbon atoms, further more preferably from 3 to 20 carbonatoms, and especially preferably from 6 to 20 carbon atoms; for example,a triphenylphosphine ligand, etc.), thiolate ligands (preferablythiolate ligands having from 1 to 30 carbon atoms, more preferably from1 to 20 carbon atoms, and further more preferably from 6 to 20 carbonatoms; for example, a phenylthiolate ligand, etc.) and phosphine oxideligands (preferably phosphine oxide ligands having from 3 to 30 carbonatoms, more preferably from 8 to 30 carbon atoms, and further morepreferably from 18 to 30 carbon atoms; for example, a triphenylphosphineoxide ligand, etc.), with nitrogen-containing heterocyclic ligands beingmore preferable.

The complex may contain one transition metal atom in the compoundthereof, or may be a so-called polynuclear complex containing two ormore transition metal atoms therein. The complex may contain metal atomsof a different kind at the same time.

Among them, specific examples of the light emitting material include,for example, U.S. Pat. No. 6,303,238B1, U.S. Pat. No. 6,097,147, WO00/57676, WO 00/70655, WO 01/08230, WO 01/39234A2, WO 01/41512A1, WO02/02714A2, WO 02/15645A1, WO 02/44189A1, WO 05/19373A2,JP-A-2001-247859, JP-A-2002-302671, JP-A-2002-117978, JP-A-2003-133074,JP-A-2002-235076, JP-A-2003-123982, JP-A-2002-170684, EP1211257,JP-A-2002-226495, JP-A-2002-234894, JP-A-2001-247859, JP-A-2001-298470,JP-A-2002-173674, JP-A-2002-203678, JP-A-2002-203679, JP-A-2004-357791,JP-A-2006-256999, JP-A-2007-19462, JP-A-2007-84635, JP-A-2007-96259,etc. Above all, more preferred examples of the light emitting materialinclude Ir complexes, Pt complexes, Cu complexes, Re complexes, Wcomplexes, Rh complexes, Ru complexes, Pd complexes, Os complexes, Eucomplexes, Tb complexes, Gd complexes, Dy complexes and Ce complexes. Inparticular, Ir complexes, Pt complexes and Re complexes are preferable;and Ir complexes, Pt complexes and Re complexes containing at least onecoordination mode of a metal-carbon bond, a metal-nitrogen bond, ametal-oxygen bond and a metal-sulfur bond are more preferable.Furthermore, from the viewpoints of luminous efficiency, drivingdurability, chromaticity, etc., Ir complexes, Pt complexes and Recomplexes each containing a tridentate or multidentate ligand areespecially preferable, with Ir complexes and Pt complexes being the mostpreferable. Above all, Pt complexes containing a tetradentate ligand areespecially preferable.

Though the light emitting material is not particularly limited, it ispreferred to use a phosphorescent material; it is more preferred to usean iridium complex phosphorescent material or a platinum complexphosphorescent material; and it is especially preferred to use aplatinum complex phosphorescent material having a tetradentate ligand.Other phosphorescent material may be used jointly.

Examples of the complex phosphorescent material include compoundsdescribed in Coordination Chemistry Reviews, 250 (2006), pages 2093 to2126.

Examples of the iridium complex phosphorescent material includecompounds disclosed in WO 00/70655, WO 01/41512, WO 02/5645,JPA-2002-117978, WO 04/085450, WO 06/121811, WO 05/019373 and WO05/113704.

Examples of the platinum complex phosphorescent material includecompounds disclosed in WO 00/57676.

More specifically, as the platinum complex (phosphorescent) materialhaving a tetradentate ligand, compounds disclosed in U.S. Pat. No.6,653,654, WO 2004/099339, WO 04/108857, JP-A-2005-310733,JP-A-2005-317516, JP-A-2006-261623, JP-A-2006-93542, JP-A-2006-256999,WO 06/098505, JP-A-2007-19462, JP-A-2007-96255, JP-A-2007-96259, WO05/042444, JP-A-2006-232784 and WO 05/042550 are preferable.

The platinum complex (phosphorescent) materials having tetradentateligands are preferably those containing 2-arylpyridine derivatives,2-(1-pyrazolyl)pyridine derivatives or 1-arylpyrazole derivatives aspartial structures of their respective ligands, more preferably thosecontaining 2-arylpyridine derivatives or 2-(1-pyrazolyl)pyridinederivatives as partial structures of their respective ligands,especially preferably those containing 2-arylpyridine derivatives aspartial structures of their respective ligands.

Also, the partial structures of ligands (for example, 2-arylpyridinederivatives, 2-(1-pyrazolyl)pyridine derivatives, 1-arylpyrazolederivatives, etc.) are linked together at their appropriate sites andform a tetradentate ligand.

In the case of containing 2-arylpyridine derivatives as partialstructures of a ligand, it is preferable that the linking site of eachderivative is the 6-position of the pyridine ring or the aryl carbon inthe position meta to the pyridine ring; it is more preferable that theirpyridine rings are linked at the 6-position each other or their arylcarbons in the positions meta to the pyridine rings are linked; and itis especially preferable that their pyridine rings are linked at the6-position each other.

In the case of containing 2-(1-pyrazolyl)pyridine derivatives as partialstructures of a ligand, it is preferable that the linking site of eachderivative is the 6-position of the pyridine ring or the 4-position ofthe 1-pyrazolyl group; it is more preferable that their pyridine ringsare linked at the 6-position each other or their 1-pyrazolyl groups arelinked at the 4-position each other; and it is especially preferablethat their pyridine rings are linked at the 6-position each other.

In the case of containing 1-arylpyrazole derivatives as partialstructures of a ligand, it is preferable that the linking site of eachderivative is the 3-position of the pyrazole ring or the aryl carbon inthe position meta to the pyrazole ring; it is more preferable that theirpyrazole rings are linked at the 3-position each other or their arylcarbons in the positions meta to the pyrazole rings are linked; and itis especially preferable that their pyrazole rings are linked at the3-position each other.

Though a structure for linking the foregoing partial structure of theligand may be either a single bond or a divalent linking group, it ispreferably a divalent linking group. As the divalent linking group, forexample, a methylene linkage, an ethylene linkage, a phenylene linkage,a nitrogen atom linkage, an oxygen atom linkage, a sulfur atom linkageand a silicon atom linkage are preferable; a methylene linkage, anitrogen atom linkage and a silicon atom linkage are more preferable;and a methylene linkage is especially preferred. Specific examples ofthe methylene linking group include a methylene group (—CH₂—), amethylmethylene group (—CHMe—), a fluoromethylmethylene group (—CFMe—),a dimethylmethylene group (—CMe₂-), a methylphenylmethylene group(—CMePh-), a diphenylmethylene group (—CPh₂-), a 9,9-fluorenediyl group,a 1,1-cyclopentadiyl group and a 1,1-cyclohexanediyl group. Of these, adimethylmethylene group, a diphenylmethylene group, a 9,9-fluorenediylgroup, a 1,1-cyclopentanediyl group and a 1,1-cyclohexanediyl group arepreferable; a dimethylmethylene group, a diphenylmethylene group and a1,1-cyclohexanediyl group are more preferable; and a dimethylmethylenegroup is especially preferable.

Also, one of complexes which are more preferable as the platinum complex(phosphorescent) material having a tetradentate ligand is a Pt complexrepresented by the following formula (A).

In the formula (A), each of R^(A3) and R^(A4) independently represents ahydrogen atom or a substituent; and each of R^(A1) and R^(A2)independently represents a substituent. In the case of containing aplurality of each of R^(A1) and R^(A2), each R^(A1) may be the same asor different from every other R^(A1) and may be linked to each other toform a ring; and each R^(A2) may be the same as or different from everyother R^(A2) and may be linked to each other to form a ring. Each ofn^(A1) and n^(A2) independently represents an integer of from 0 to 4.Y^(A1) represents a linking group.

The substituent represented by each of R^(A1), R^(A2), R^(A3) and R^(A4)may be arbitrarily chosen among those which are exemplified previouslyas the group A of substituent.

The linking group represented by Y^(A1) may be arbitrarily chosen amongthose which are exemplified below as the following group A of linkinggroup.

(Group A of Linking Group)

Examples of the group A of linking group include an alkylene group (forexample, methylene, ethylene, propylene, etc.), an arylene group (forexample, phenylene, naphthalenediyl, etc.), a heteroarylene group (forexample, pyridinediyl, thiophenediyl, etc.), an imino group (—NR—) (forexample, a phenylimino group, etc.), an oxy group (—O—), a thio group(—S—), a phosphinidene group (—PR—) (for example, a phenylphosphinidenegroup, etc.), a silylene group (—SiRR′—) (for example, adimethylsilylene group, a diphenylsilylene group, etc.) and acombination thereof. Each of these linking groups may further have asubstituent.

As the substituent represented by each of R^(A1), R^(A2), R^(A3) andR^(A4), an alkyl group, an aryl group and a heterocyclic group arepreferable; an aryl group and a heterocyclic group are more preferable;and an aryl group is especially preferable.

The linking group represented by Y^(A1) is preferably a vinyl groupsubstituted at the 1- and 2-positions, a phenylene ring, a pyridinering, a pyrazine ring, a pyrimidine ring or an alkylene group havingfrom 1 to 8 carbon atoms; more preferably a vinyl group substituted atthe 1- and 2-positions, a phenylene ring or an alkylene group havingfrom 1 to 6 carbon atoms; and especially preferably a phenylene ring.

The substituent represented by each of R^(A3) and R^(A4) may be linkedto the linking group represented by Y^(A1) to form a ring. For example,in the case of a phenylene ring in which Y^(A1) is linked at the 1- and2-positions, R^(A3) and R^(A4) may be linked at the 3- and 6-positions,respectively to form a 1,10-phenanthroline ring, which may further havea substituent.

One of complexes which are more preferable as the platinum complex(phosphorescent) material having a tetradentate ligand is a Pt complexrepresented by the following formula (B).

In the formula (B), each of A^(B1) and A^(B6) independently representsC—R or N. R represents a hydrogen atom or a substituent. L^(B1)represents a single bond or a divalent linking group. X represents C orN. Z represents a 5-membered or 6-membered aromatic ring or aromaticheterocyclic ring which is formed together with X—C in the formula.Q^(B1) represents an anionic group which is bound to Pt.

The formula (B) is described.

Each of A^(B1) to A^(B6) independently represents C—R or N. R representsa hydrogen atom or a substituent. The substituent represented by R issynonymous with that exemplified previously as the group A ofsubstituent, and a preferred range is also the same.

Each of A^(B1) to A^(B6) is preferably C—R, and Rs may be linked to eachother to form a ring. In the case where each of A^(B1) to A^(B6) is C—R,R in each of A^(B2) and A^(B5) is preferably a hydrogen atom, an alkylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,a fluorine group or a cyano group, more preferably a hydrogen atom, anamino group, an alkoxy group, an aryloxy group or a fluorine group, andespecially preferably a hydrogen atom or a fluorine group; and R in eachof A^(B1), A^(B3), A^(B4) and A^(B6) is a hydrogen atom, an alkyl group,an aryl group, an amino group, an alkoxy group, an aryloxy group, afluorine group or a cyano group, more preferably a hydrogen atom, anamino group, an alkoxy group, an aryloxy group or a fluorine group, andespecially preferably a hydrogen atom.

L^(B1) represents a single bond or a divalent linking group.

Examples of the divalent linking group represented by L^(B1) include analkylene group (for example, methylene, ethylene, propylene, etc.), anarylene group (for example, phenylene, naphthalenediyl, etc.), aheteroarylene group (for example, pyridinediyl, thiophenediyl, etc.), animino group (—NR—) (for example, a phenylimino group, etc.), an oxygroup (—O—), a thio group (—S—), a phosphinidene group (—PR—) (forexample, a phenylphosphinidene group, etc.), a silylene group (—SiRR′—)(for example, a dimethylsilylene group, a diphenylsilylene group, etc.)and a combination thereof. Each of these linking groups may further havea substituent.

L^(B1) is preferably a single bond, an alkylene group, an arylene group,a heteroarylene group, an imino group, an oxy group, a thio group or asilylene group; more preferably a single bond, an alkylene group, anarylene group or an imino group; further more preferably an alkylenegroup; still further more preferably a methylene group; even furthermore preferably a disubstituted methylene group; even still further morepreferably a dimethylmethylene group, a diethylmethylene group, adiisobutylmethylene group, a dibenzylmethylene group, anethylmethylmethylene group, a methylpropylmethylene group, anisobutylmethylmethylene group, a diphenylmethylene group, amethylphenylmethylene group, a cyclohexanediyl group, a cyclopentanediylgroup, a fluorenediyl group or a fluoromethylmethylene group; andespecially preferably a dimethylmethylene group, a diphenylmethylenegroup or a cyclohexanediyl group.

X represents C or N. Z represents a 5-membered or 6-membered aromatichydrocarbon ring or aromatic heterocyclic ring formed together with X—Cin the formula. Examples of the aromatic hydrocarbon ring or aromaticheterocyclic ring represented by Z include a benzene ring, a naphthalenering, an anthracene ring, a pyrene ring, a phenanthrene ring, a perylenering, a pyridine ring, a quinoline ring, an isoquinoline ring, aphenanthridine ring, a pyrimidine ring, a pyrazine ring, a pyridazinering, a triazine ring, a cinnoline ring, an acridine ring, a phthalazinering, a quinazoline ring, a quinoxaline ring, a naphthyridine ring, apteridine ring, a pyrrole ring, a pyrazole ring, a triazole ring, anindole ring, a carbazole ring, an indazole ring, a benzimidazole ring,an oxazole ring, a thiazole ring, an oxadiazole ring, a thiadiazolering, a benzoxazole ring, a benzothiazole ring, an imidazopyridine ring,a thiophene ring, a benzothiophene ring, a furan ring, a benzofuranring, a phosphole ring, a phosphinine ring and a silole ring. Z may havea substituent. As the substituent, those which are exemplifiedpreviously as the group A of substituent are applicable. Also, Z mayform a condensed ring together with other ring.

Z is preferably a benzene ring, a naphthalene ring, a pyrazole ring, animidazole ring, a triazole ring, a pyridine ring, an indole ring or athiophene ring, and more preferably a benzene ring, a pyrazole ring or apyridine ring.

Q^(B1) represents an anionic group which is bound to Pt. Examples of theanionic group represented by Q^(B1) include a vinyl ligand, an aromatichydrocarbon ring ligand (for example, a benzene ligand, a naphthaleneligand, an anthracene ligand, a phenanthracene ligand, etc.) and aheterocyclic ligand (for example, a furan ligand, a thiophene ligand, apyridine ligand, a pyrazine ligand, a pyrimidine ligand, a pyridazineligand, a triazine ligand, a thiazole ligand, an oxazole ligand, apyrrole ligand, an imidazole ligand, a pyrazole ligand, a triazoleligand and a condensed ring ligand containing the foregoing ligand (forexample, a quinoline ligand, a benzothiazole ligand, etc.), etc.).Herein, the bond between Q^(B1) and Pt may be any of a covalent bond, anionic bond or a coordinate bond. The atom bound to Pt in Q^(B1) ispreferably a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atomor a phosphorus atom, more preferably a carbon atom, an oxygen atom or anitrogen atom, and further more preferably a carbon atom.

The group represented by Q^(B1) is preferably an aromatic hydrocarbonring ligand which is bound to Pt via its carbon atom, an aromaticheterocyclic ligand which is bound to Pt via its carbon atom, anitrogen-containing aromatic heterocyclic ligand which is bound to Ptvia its nitrogen atom or an acyloxy ligand; and more preferably anaromatic hydrocarbon ring ligand which is bound to Pt via its carbonatom or an aromatic heterocyclic ligand which is bound to Pt via itscarbon atom. It is especially preferable that the group represented byQ^(B1) is the same group as that in the ring Z formed together with C—Xin the formula (B).

The Pt complex represented by the formula (B) is more preferably a Ptcomplex represented by the following formula (C).

In the formula (C), each of A^(C1) to A^(C14) independently representsC—R or N. R represents a hydrogen atom or a substituent. L^(C1)represents a single bond or a divalent linking group.

The formula (C) is described.

Each of A^(C1) to A^(C14) independently represents C—R or N. Rrepresents a hydrogen atom or a substituent. A^(C1) to A^(C6) arerespectively synonymous with A^(B1) to A^(B6) in the foregoing formula(B), and preferred ranges thereof are also the same.

As to A^(C7) to A^(C14), a number of Ns (nitrogen atoms) in each ofA^(C7) to A^(C10) and A^(C11) to A^(C14) is preferably from 0 to 2, andmore preferably from 0 or 1. The ring constituent N is chosen preferablyamong A^(C8) to A^(C10) and A^(C12) to A^(C14), more preferably amongA^(C8), A^(C9), A^(C12) and A^(C13), and especially preferably fromA^(C8) or A^(C12).

When each of A^(C7) to A^(C14) represents C—R, R of each of A^(C8) andA^(C12) is preferably a hydrogen atom, an alkyl group, a polyfluoroalkylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,a fluorine group or a cyano group, more preferably a hydrogen atom, apolyfluoroalkyl group, an alkyl group, an aryl group, a fluorine groupor a cyano group, and especially preferably a hydrogen atom, apolyfluoroalkyl group or a cyano group. R of each of A^(C7), A^(C9),A^(C11) and A^(C13) is preferably a hydrogen atom, an alkyl group, apolyfluoroalkyl group, an aryl group, an amino group, an alkoxy group,an aryloxy group, a fluorine group or a cyano group, more preferably ahydrogen atom, a polyfluoroalkyl group, a fluorine group or a cyanogroup, and especially preferably a hydrogen atom or a fluorine group. Rof each of A^(C10) and A^(C14) is preferably a hydrogen atom or afluorine group, and more preferably a hydrogen atom. When any one ofA^(C7) to A^(C9) or A^(C11) to A^(C13) represents C—R, Rs may be linkedto each other to form a ring.

The linking group represented by L^(C1) is synonymous with the likinggroup represented by L^(B1) in the foregoing formula (B), and apreferred range thereof is also the same.

The Pt complex represented by the formula (B) is further more preferablya Pt complex represented by the following formula (D).

In the formula (D), each of A^(D1) to A^(D12) independently representsC—R or N. R represents a hydrogen atom or a substituent. L^(D1)represents a single bond or a divalent linking group.

The formula (D) is described.

Each of A^(D1) to A^(D12) independently represents C—R or N. Rrepresents a hydrogen atom or a substituent.

A^(D1) to A^(D6) are respectively synonymous with A^(B1) to A^(B6) inthe foregoing formula (B), and preferred ranges thereof are also thesame.

As to A^(D7) to A^(C12), a number of Ns (nitrogen atoms) in each ofA^(D7) to A^(D9) and A^(D10) to A^(D12) is preferably from 0 to 2, morepreferably from 0 or 1, and especially preferably 1. The ringconstituent N is chosen preferably among A^(D7) to A^(D9) and A^(D10) toA^(D12), more preferably among A^(D7), A^(D9), A^(D10) and A^(D12), andespecially preferably from A^(D7) or A^(D10).

When each of A^(D7) to A^(D12) represents C—R, R of each of A^(D8) andA^(D11) is preferably a hydrogen atom, an alkyl group, a polyfluoroalkylgroup, an aryl group, an amino group, an alkoxy group, an aryloxy group,a fluorine group or a cyano group, more preferably a hydrogen atom, apolyfluoroalkyl group, an alkyl group, an aryl group, a fluorine groupor a cyano group, and especially preferably a polyfluoroalkyl group (forexample, a trifluoromethyl group, a perfluoroethyl group, etc.) or acyano group. R of each of A^(D7), A^(D9), A^(D10) and A^(D12) ispreferably a hydrogen atom, an alkyl group, a polyfluoroalkyl group, anaryl group, an amino group, an alkoxy group, an aryloxy group, afluorine group or a cyano group, and more preferably a hydrogen atom ora fluorine group. When any one of A^(D7) to A^(D12) represents C—R, Rsmay be linked to each other to form a ring.

The linking group represented by L^(D1) is synonymous with the linkinggroup represented by L^(B1) in the foregoing formula (B), and apreferred range thereof is also the same.

One of complexes which are more preferable as the platinum complex(phosphorescent) material having a tetradentate ligand is a Pt complexrepresented by the following formula (E).

In the formula (E), each of A^(E1) to A^(E14) independently representsC—R or N. R represents a hydrogen atom or a substituent. L^(E1)represents a single bond or a divalent linking group.

The formula (E) is described. Each of A^(E1) to A^(E14) independentlyrepresents C—R or N. R represents a hydrogen atom or a substituent.A^(E1) to A^(E6) are respectively synonymous with A^(B1) to A^(B6) inthe foregoing formula (B), and preferred ranges thereof are also thesame. A^(E7) to A^(E14) are respectively synonymous with A^(C7) toA^(C14) in the foregoing formula (C), and preferred ranges thereof arealso the same.

The linking group represented by L^(E1) is synonymous with the linkinggroup represented by L^(B1) in the foregoing formula (B), and apreferred range thereof is also the same.

L^(E1) is preferably a single bond, an alkylene group, an arylene group,a heteroarylene group, an imino group, an oxy group, a thio group or asilylene group; more preferably an alkylene group, an imino group, anoxy group, a thio group or a silylene group; further more preferably analkylene group; even further more preferably a methylene group; evenfurther more preferably a disubstituted methylene group; even stillfurther more preferably a dimethylmethylene group, a diethylmethylenegroup, a diisobutylmethylene group, a dibenzylmethylene group, anethylmethylmethylene group, a methylpropylmethylene group, anisobutylmethylmethylene group, a diphenylmethylene group, amethylphenylmethylene group, a cyclohexanediyl group, a cyclopentanediylgroup, a fluorenediyl group or a fluoromethylmethylene group; andespecially preferably a dimethylmethylene group, a diphenylmethylenegroup or a cyclohexanediyl group.

One of complexes which are more preferable as the platinum complex(phosphorescent) material having a tetradentate ligand is a Pt complexrepresented by the following formula (F).

In the formula (F), each of A^(F1) to A^(F14) independently representsC—R or N. R represents a hydrogen atom or a substituent. L^(F1)represents a single bond or a divalent linking group.

The formula (F) is described.

Each of A^(F1) to A^(F14) independently represents C—R or N. Rrepresents a hydrogen atom or a substituent. A^(F1) to A^(F5) arerespectively synonymous with A^(B1) to A^(B5) in the foregoing formula(B). Each of A^(F1) to A^(F5) is preferably C—R, and Rs may be linked toeach other to form a ring. When each of A^(F1) to A^(F5) is C—R, R ofeach of A^(F1) to A^(F5) is preferably a hydrogen atom, an alkyl group,an aryl group, an amino group, an alkoxy group, an aryloxy group, afluorine group or a cyano group, more preferably a hydrogen atom, anaryl group, a fluorine group or a cyano group, and especially preferablya hydrogen atom.

A^(F7) to A^(F14) are respectively synonymous with A^(C7) to A^(C14) inthe foregoing formula (C), and preferred ranges thereof are also thesame. In particular, when any one of A^(F7) to A^(F9) or A^(F11) toA^(F13) represents C—R, Rs may be linked to each other to form a ring.The ring structure formed when Rs are linked to each other is preferablya furan ring, a benzofuran ring, a pyrrole ring, a benzopyrrole ring, athiophene ring, a benzothiophene ring or a fluorene ring. Each of theserings may further have a substituent.

The linking group represented by L^(F1) is synonymous with the linkinggroup represented by L^(B1) in the foregoing formula (B), and apreferred range thereof is also the same.

Specific examples of the light emitting material are given below, but itshould not be construed that the invention is limited thereto.

Also, examples of the platinum complex phosphorescent material having atetradentate ligand are given below, but it should not be construed thatthe invention is limited thereto.

The light emitting material is generally contained in an amount of from0.1% by mass to 50% by mass relative to the mass of all the compoundscapable for forming the light emitting layer. From the viewpoints ofdurability and external quantum efficiency, a content of the lightemitting material is preferably from 1% by mass to 50% by mass, and morepreferably from 2% by mass to 40% by mass.

<<Host Material>>

Examples of the host material which is contained in the light emittinglayer include, in addition to the compound of the invention, a materialhaving a carbazole skeleton, a material having an azacarbazole skeleton,a material having an indole skeleton, a material having an azaindoleskeleton, a material having a diarylamine skeleton, a material having apyridine skeleton, a material having a pyrazine skeleton, a materialhaving a triazine skeleton, a material having an arylsilane skeleton andmaterials exemplified in the sections of a hole injection layer, a holetransport layer, an electron injection layer and an electron transportlayer as described later.

Though a content of the host material is not particularly limited, it ispreferably from 50 to 99% by mass, more preferably from 70 to 95% bymass, and especially preferably from 85 to 90% by mass relative to thewhole mass of the materials to be contained in the light emitting layer.

The thickness of the light emitting layer is not particularly limited.In general, the thickness of the light emitting layer is preferably from1 nm to 500 nm, more preferably from 5 nm to 200 nm, and furtherpreferably from 10 nm to 100 nm.

—Hole Injection Layer and Hole Transport Layer—

Each of the hole injection layer and the hole transport layer is a layerhaving a function to accept a hole from the anode or the anode side totransport it into the cathode side. Specifically, each of the holeinjection layer and the hole transport layer is preferably a layercontaining, in addition to the compound of the invention, a carbazolederivative, an azacarbazole derivative, an indole derivative, anazaindole derivative, a triazole derivative, an oxazole derivative, anoxadiazole derivative, an imidazole derivative, a polyarylalkanederivative, a pyrazoline derivative, a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, a styrylanthracene derivative, afluorenone derivative, a hydrazone derivative, a stilbene derivative, asilazane derivative, an aromatic tertiary amine compound, a styrylaminecompound, an aromatic dimethylidine based compound, a porphyrin basedcompound, an organic silane derivative, carbon or the like.

The thickness of each of the hole injection layer and the hole transportlayer is preferably not more than 500 nm from the viewpoint of loweringthe driving voltage.

The thickness of the hole transport layer is preferably from 1 nm to 500nm, more preferably from 5 nm to 200 nm, and further preferably from 10nm to 100 nm. Also, the thickness of the hole injection layer ispreferably from 0.1 nm to 200 nm, more preferably from 0.5 nm to 100 nm,and further preferably from 1 nm to 100 nm.

Each of the hole injection layer and the hole transport layer may be ofa single layer structure composed of one or two or more kinds of theforegoing materials or may be of a multilayer structure composed of aplurality of layers of the same or different compositions.

—Electron Injection Layer and Electron Transport Layer—

Each of the electron injection layer and the electron transport layer isa layer having a function to accept an electron from the cathode or thecathode side and to transport it into the anode side. Specifically, eachof the electron injection layer and the electron transport layer ispreferably a layer containing, in addition to the compounds of thepresent invention, a triazole derivative, an oxazole derivative, anoxadiazole derivative, an imidazole derivative, a fluorenone derivative,an anthraquinodimethane derivative, an anthrone derivative, adiphenylquinone derivative, a thiopyrandioxide derivative, acarbodiimide derivative, a fluorenylidenemethane derivative, adistyrylpyrazine derivative, an aromatic tetracarboxylic acid anhydrideof naphthalene, perylene, etc., a phthalocyanine derivative, a metalcomplex of every sort represented by metal complexes of an 8-quinolinolderivative and metal complexes containing, as a ligand, metalphthalocyanine, benzoxazole or benzothiazole, an organic silanederivative, or the like.

The thickness of each of the electron injection layer and the electrontransport layer is preferably not more than 500 nm from the viewpoint oflowering the driving voltage.

The thickness of the electron transport layer is preferably from 1 nm to500 nm, more preferably from 5 nm to 200 nm, and further preferably from10 nm to 100 nm. Also, the thickness of the electron injection layer ispreferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm,and further preferably from 0.5 nm to 50 nm.

Each of the electron injection layer and the electron transport layermay be of a single layer structure composed of one or two or more kindsof the foregoing materials or may be of a multilayer structure composedof a plurality of layers of the same or different compositions.

—Hole Blocking Layer—

The hole blocking layer is a layer having a function to preventpermeation of the hole having been transported from the anode side tothe light emitting layer into the cathode side. In the invention, thehole blocking layer can be provided as an organic compound layeradjacent to the light emitting layer on the cathode side.

Examples of the organic compound constituting the hole blocking layerinclude, in addition to the compound of the invention, aluminumcomplexes such as BAlq, triazole derivatives and phenanthrolinederivatives such as BCP.

The thickness of the hole blocking layer is preferably from 1 nm to 500nm, more preferably from 5 nm to 200 nm, and further preferably from 10nm to 100 nm.

The hole blocking layer may be of a single layer structure composed ofone or two or more kinds of the foregoing materials or may be of amultilayer structure composed of a plurality of layers of the same ordifferent compositions.

—Electron Blocking Layer—

The electron blocking layer is a layer having a function of preventingpassage of an electron, which has been transported to the light emittinglayer from the cathode side, to the anode side. In the invention, theelectron blocking layer may be provided as an organic layer adjacent tothe light emitting layer on the anode side.

Examples of the compound constituting the electron blocking layerinclude those exemplified previously as the hole transporting material.

A thickness of the electron blocking layer is preferably from 1 nm to500 nm, more preferably from 5 nm to 200 nm, and further more preferablyfrom 10 nm to 100 nm.

The electron blocking layer may be of a single-layered structurecomposed of one or two or more kinds of the foregoing materials or amultilayered structure composed of a plurality of layers having the samecomposition or a different composition from each other.

<Protective Layer>

The whole of the organic EL device may be protected by a protectivelayer.

As a material to be contained in the protective layer, any materialhaving a function to inhibit the incorporation of a substance promotingthe deterioration of the device, such as moisture and oxygen, into thedevice is useful.

Specific examples thereof include metals (for example, In, Sn, Pb, Au,Cu, Ag, Al, Ti, Ni, etc.), metal oxides (for example, MgO, SiO, SiO₂,Al₂O₃, GeO, NiO, CaO, BaO, Fe₂O₃, Y₂O₃, TiO₂, etc.), metal nitrides (forexample, SiN_(x), SiN_(x)O_(y), etc.), metal fluorides (for example,MgF₂, LiF, AlF₃, CaF₂, etc.), polyethylene, polypropylene, polymethylmethacrylate, polyimides, polyureas, polytetrafluoroethylene,polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymers ofchlorotrifluoroethylene and dichlorodifluoroethylene, copolymersobtained by copolymerizing a monomer mixture containingtetrafluoroethylene and at least one comonomer, fluorine-containingcopolymers having a cyclic structure in a copolymer main chain thereof,water-absorbing substances having a water absorption factor of 1% ormore and moisture-proof substances having a water absorption factor ofnot more than 0.1%.

A method for forming the protective layer is not particularly limited.For example, a vacuum vapor deposition process, a sputtering process, areactive sputtering process, an MBE (molecular beam epitaxy) process, acluster ion beam process, an ion plating process, a plasmapolymerization process (high-frequency exciting ion plating process), aplasma CVD process, a laser CVD process, a thermal CVD process, a gassource CVD process, a coating process, a printing process and a transferprocess can be adopted.

<Sealing Vessel>

Further, the organic EL device of the invention may be prepared bysealing the whole of the device using a sealing vessel. In addition, amoisture absorber or an inert liquid may be charged in a space betweenthe sealing vessel and the organic EL device. Though the moistureabsorber is not particularly limited, examples thereof include bariumoxide, sodium oxide, potassium oxide, calcium oxide, sodium sulfate,calcium sulfate, magnesium sulfate, phosphorus pentoxide, calciumchloride, magnesium chloride, copper chloride, cesium fluoride, niobiumfluoride, calcium bromide, vanadium bromide, molecular sieve, zeoliteand magnesium oxide. Though the inert liquid is not particularlylimited, examples thereof include paraffins, liquid paraffins, fluorinebased solvents such as perfluoroalkanes, perfluoroamines andperfluoroethers, chlorine based solvents and silicon oils.

Also, a method for sealing with a resin sealing layer as described belowis suitably adopted.

(Resin Sealing Layer)

It is preferred to suppress deterioration of performances of thefunctional device of the invention, which is caused due to contact withoxygen or moisture in the atmosphere by a resin sealing layer.

(Material)

A resin material for the resin sealing layer is not particularlylimited, and acrylic resins, epoxy resins, fluorine based resins,silicon based resins, rubber based resins, ester based resins and so onare useful. Of these, epoxy resins are preferable from the standpoint ofa moisture preventive function thereof. Of the epoxy resins,thermosetting epoxy resins and photocurable epoxy resins are preferable.

(Preparation Method)

A method for preparing a resin sealing layer is not particularlylimited, and examples thereof include a method for coating a resinsolution, a method for press bonding or hot press bonding of a resinsheet and a method for dry polymerization by vapor deposition,sputtering or the like.

(Film Thickness)

A thickness of the resin sealing layer is preferably 1 μm or more andnot more than 1 mm, more preferably 5 μm or more and not more than 100μm, and most preferably 10 μm or more and not more than 50 μm. When thethickness of the resin sealing layer is thinner than the foregoingrange, there is a concern that the inorganic film is damaged at the timeof mounting a second substrate. On the other hand, when the thickness ofthe resin sealing layer is thicker than the foregoing range, a thicknessof the electroluminescence device itself becomes thick, therebyimpairing characteristic features of the organic electroluminescencedevice, that is, thin film properties.

(Sealing Adhesive)

A sealing adhesive which is used in the invention has a function ofpreventing intrusion of moisture or oxygen from the edge.

(Material)

As a material for the sealing adhesive, the same materials as those usedfor the resin sealing layer are useful. Of these, epoxy based adhesivesare preferable from the standpoint of preventing intrusion of moisture,and photocurable adhesives or thermosetting adhesives are especiallypreferable.

Also, it is preferred to add a filler to the foregoing material.

The filler which is added to the sealing agent is preferably aninorganic material such as SiO₂, SiO (silicon oxide), SiON (siliconoxynitride) and SiN (silicon nitride). The addition of the fillerincreases a viscosity of the sealing agent, thereby enhancing processingadaptability and enhancing humidity resistance.

(Drying Agent)

The sealing adhesive may contain a drying agent. The drying agent ispreferably barium oxide, calcium oxide or strontium oxide.

The addition amount of the drying agent is preferably 0.01% by mass ormore and not more than 20% by mass, and more preferably 0.05% by mass ormore and not more than 15% by mass relative to the sealing adhesive.When the addition amount of the drying agent is less than the foregoingrange, addition effects of the drying agent become insufficient. On theother hand, what the addition amount of the drying agent exceeds theforegoing range is not preferable because it is difficult to uniformlydisperse the drying agent in the sealing adhesive.

(Formulation of Sealing Adhesive)

Polymer Composition and Concentration:

The sealing adhesive is not particularly limited, and those describedpreviously are useful. Examples of the photocurable epoxy adhesiveinclude XNR5516, manufactured by Nagase Chemtex Corporation. The sealingadhesive may be prepared by adding the drying agent directly to thesealing adhesive and then dispersing the resulting mixture.

Thickness:

A coating thickness of the sealing adhesive is preferably 1 μm or moreand not more than 1 mm. What the coating thickness of the sealingadhesive is thinner than the foregoing range is not preferable becausethe sealing adhesive cannot be uniformly coated. On the other hand, whatthe coating thickness of the sealing adhesive exceeds the foregoingrange is not preferable, too because a moisture intrusion path becomeswide.

(Sealing Method)

In the invention, the functional device is able to be obtained bycoating an arbitrary amount of the sealing adhesive having the dryingagent incorporated therein by using a disperser or the like, thensuperimposing a second substrate thereon and thereafter curing thestack.

[Driving]

According to the organic EL device of the invention, light emission canbe obtained by applying a voltage of direct current (optionallycontaining an alternating current component) (usually from 2 volts to 15volts) or a current of direct current between the anode and the cathode.

As to the driving method of the organic EL device of the invention,driving methods disclosed in JP-A-2-148687, JP-A-6-301355, JP-A-5-29080,JP-A-7-134558, JP-A-8-234685, JP-A-8-241047, Japanese Patent No. 2784615and U.S. Pat. Nos. 5,828,429 and 6,023,308 can be applied.

[Application of the Present Invention]

The organic electroluminescence device of the invention can be suitablyutilized for display devices, displays, backlights, electrophotography(xerography), illumination light sources, recording light sources,exposure light sources, read light sources, markers, signboards,interiors, optical communications and so on.

EXAMPLES

The invention is hereunder described in detail with reference to thefollowing Examples, but it should not be construed that the invention islimited thereto.

Synthesis Example 1 Synthesis of Illustrative Compound 1

Illustrative Compound 1 may be synthesized according to the followingscheme.

Compound A was obtained in a yield of 82% by heat refluxing carbazoleand 1-fluoro-2-nitrobenzene in the coexistence of potassium carbonatefor 4 hours. The Compound A was reduced with a tin powder and convertedinto Compound B in a yield of 89%. The Compound B was allowed to reactwith sodium nitrite in a solvent of sulfuric acid (concentration: 18% byvolume) and acetic acid (concentration: 82% by volume) at 0° C. and thencondensed by means of heat decomposition, thereby obtaining Compound Cin a yield of 62%. The Compound C was brominated in chloroform to obtainCompound D in a yield of 56%. The Compound D was allowed to react withnormal butyllithium in a THF solvent. Triphenylchlorosilane was addedthereto, and the mixture was allowed to react at room temperature forone hour. The reaction mixture was hydrolyzed with a sodiumhydrogencarbonate aqueous solution, thereby obtaining IllustrativeCompound 1 in a yield of 27%.

¹H-NMR data of Illustrative Compound 1: (400 MHz, CDCl₃): δ/ppm 8.24 (s,2H), 8.07 (d, J=7.5 Hz, 2H), 7.92 (d, J=8.05 Hz, 2H), 7.72 to 7.75 (m,6H), 7.58 to 7.52 (m, 2H), 7.49 to 7.38 (m, 9H), 7.36 to 7.30 (m, 2H)

Preparation of Organic Electroluminescence Device Comparative Example1-1

A washed ITO substrate was put into a vapor deposition apparatus; copperphthalocyanine was vapor deposited thereon in a thickness of 10 nm; andNPD ((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 40 nm. Compound A-1 and Compound Bwere vapor deposited thereon at a ratio of 12/88 (mass ratio) in athickness of 30 nm (light emitting layer); BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of30 nm; and Alq (tris(8-hydroxyquinoline)aluminum complex) was thenadditionally vapor deposited thereon in a thickness of 10 nm (electrontransport layer). After vapor depositing thereon lithium fluoride in athickness of 3 nm, aluminum was vapor deposited in a thickness of 60 nm.The resultant was put into a glove box purged with an argon gas withoutbeing brought into contact with the air and sealed in a sealing can madeof stainless steel with a UV-curable adhesive (XNR5516HV, manufacturedby Nagase-Ciba Ltd.) to obtain an organic electroluminescence device ofComparative Example 1. The EL device was subjected to light emissionupon being impressed with a direct current constant voltage using asource measure unit MODEL 2400, manufactured by Toyo Corporation. As aresult, phosphorescence derived from the Compound A-1 was obtained. Avapor deposition rate was regulated to be 0.2 nm/sec.

Also, a film thickness was calculated from a vapor deposition ratemeasured by a quartz crystal deposition controller CRTM-9000,manufactured by ULVAC, Inc. and a calibration curve prepared on thebasis of film thickness values obtained by a DEKTAK type stylus filmthickness measurer.

Examples 1-1 to 1-55 and Comparative Examples 1-2 to 1-15

Devices were prepared in the same manner as in Comparative Example 1-1,except for changing the compound used in the light emitting layer to acompound shown in Table 1 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 1.

[Evaluation of Performances of Organic Electroluminescence Device](a) External Quantum Efficiency:

Each of the devices was subjected to light emission upon being impressedwith a direct current using a source measure unit MODEL 2400,manufactured by Toyo Corporation. Its brightness was measured usingBM-8, manufactured by Topcon Corporation. An emission spectrum and anemission wavelength were measured using a spectral analyzer PMA-11,manufactured by Hamamatsu Photonics K.K. An external quantum efficiencyat a brightness in the vicinity of 1,000 cd/m² was calculated based onthese measured values according to a brightness conversion method, and arelative value thereof was determined

(b) Driving Voltage:

Each of the devices was subjected to light emission upon being impressedwith a direct current such that the brightness was 1,000 cd/m². At thattime, an impressed voltage was defined as an index for the evaluation ofdriving voltage.

TABLE 1 External quantum Difference in driving efficiency voltage fromComparative Light emitting layer (relative value) Example 1-1 (ΔV)Comparative A-1 B 1.00 — Example 1-1 Example 1-1 A-1 C-1 1.53 −0.89Example 1-2 A-1 C-2 1.44 −1.33 Example 1-3 A-1 C-3 1.32 −0.85 Example1-4 A-1 C-4 1.29 −0.93 Example 1-5 A-1 C-5 1.41 −1.15 Example 1-6 A-1C-6 1.63 −1.01 Example 1-7 A-1 C-7 1.49 −1.13 Example 1-8 A-1 C-8 1.39−0.78 Example 1-9 A-1 C-9 1.43 −0.82 Example 1-10 A-1  C-10 1.55 −0.97Example 1-11 A-1  C-11 1.38 −1.18 Comparative A-1 Illustrative Compound9 of 1.12 −0.55 Example 1-2 JP-A-2004-171808 Comparative A-1Illustrative Compound A-4 of 1.22 −0.68 Example 1-3 JP-A-2002-100467Comparative A-2 B 1.13 −0.66 Example 1-4 Example 1-12 A-2 C-1 1.73 −1.32Example 1-13 A-2 C-2 1.66 −1.92 Example 1-14 A-2 C-3 1.58 −1.29 Example1-15 A-2 C-4 1.46 −1.27 Example 1-16 A-2 C-5 1.61 −1.28 Example 1-17 A-2C-6 1.79 −1.75 Example 1-18 A-2 C-7 1.53 −1.71 Example 1-19 A-2 C-8 1.48−1.74 Example 1-20 A-2 C-9 1.62 −1.54 Example 1-21 A-2  C-10 1.68 −1.66Example 1-22 A-2 C-2 1.58 −1.84 Comparative A-2 D-1 1.23 −0.72 Example1-5 Comparative A-2 D-2 1.28 −0.88 Example 1-6 Example 1-23 A-3 C-1 1.86−1.36 Example 1-24 A-3 C-2 1.75 −1.97 Example 1-25 A-3 C-3 1.70 −1.33Example 1-26 A-3 C-4 1.53 −1.34 Example 1-27 A-3 C-5 1.74 −1.33 Example1-28 A-3 C-6 1.90 −1.80 Example 1-29 A-3 C-7 1.61 −1.73 Example 1-30 A-3C-8 1.56 −1.77 Example 1-31 A-3 C-9 1.71 −1.92 Example 1-32 A-3  C-101.73 −1.45 Example 1-33 A-3  C-11 1.66 −1.86 Comparative A-3 B 1.22−0.71 Example 1-7 Comparative A-3 D-1 1.26 −0.72 Example 1-8 ComparativeA-3 D-2 1.30 −0.87 Example 1-9 Example 1-34 A-4 C-1 1.77 −1.33 Example1-35 A-4 C-2 1.71 −1.90 Example 1-36 A-4 C-3 1.66 −1.28 Example 1-37 A-4C-4 1.44 −1.20 Example 1-38 A-4 C-5 1.69 −1.29 Example 1-39 A-4 C-6 1.80−1.71 Example 1-40 A-4 C-7 1.55 −1.67 Example 1-41 A-4 C-8 1.52 −1.62Example 1-42 A-4 C-9 1.66 −1.79 Example 1-43 A-4  C-10 1.73 −1.36Example 1-44 A-4  C-11 1.64 −1.84 Comparative A-4 B 1.17 −0.66 Example1-10 Comparative A-4 D-1 1.21 −0.68 Example 1-11 Comparative A-4 D-21.23 −0.87 Example 1-12 Example 1-45 A-5 C-1 1.91 −1.42 Example 1-46 A-5C-2 1.79 −2.05 Example 1-47 A-5 C-3 1.73 −1.38 Example 1-48 A-5 C-4 1.57−1.37 Example 1-49 A-5 C-5 1.81 −1.35 Example 1-50 A-5 C-6 1.94 −1.91Example 1-51 A-5 C-7 1.68 −1.77 Example 1-52 A-5 C-8 1.63 −1.83 Example1-53 A-5 C-9 1.82 −1.98 Example 1-54 A-5  C-10 1.83 −1.44 Example 1-55A-5  C-11 1.72 −1.98 Comparative A-5 B 1.23 −0.73 Example 1-13Comparative A-5 D-1 1.25 −0.75 Example 1-14 Comparative A-5 D-2 1.32−0.85 Example 1-15

As is clear from the foregoing results, the devices of the invention arehigh in the external quantum efficiency and low in the driving voltageas compared with the comparative devices.

Comparative Example 2-1

Similar to Comparative Example 1-1, a washed ITO substrate was put intoa vapor deposition apparatus; copper phthalocyanine was vapor depositedthereon in a thickness of 10 nm; and NPD((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 40 nm. Compound A-6 and Compound Bwere vapor deposited thereon at a ratio of 12/88 (mass ratio) in athickness of 20 nm, thereby fabricating a light emitting layer. BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of40 nm (electron transport layer). After vapor depositing thereon lithiumfluoride in a thickness of 3 nm, aluminum was vapor deposited in athickness of 60 nm to prepare a device. The EL device was subjected tolight emission upon being impressed with a direct current constantvoltage using a source measure unit MODEL 2400, manufactured by ToyoCorporation. As a result, phosphorescence derived from the Compound A-6was obtained.

Examples 2-1 to 2-16 and Comparative Examples 2-2 to 2-6

Devices were prepared in the same manner as in Comparative Example 2-1,except for changing the compound used in the light emitting layer to acompound shown in Table 2 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 2.

TABLE 2

Difference External in driving quantum voltage from Light efficiencyComparative emitting (relative Example layer value) 2-1 (ΔV) ComparativeA-6 B 1.00 — Example 2-1 Example 2-1 A-6 C-1 1.32 −1.54 Example 2-2 A-6C-3 1.24 −1.33 Example 2-3 A-6 C-5 1.37 −1.69 Example 2-4 A-6 C-6 1.41−1.58 Example 2-5 A-6 C-12 1.47 −1.72 Example 2-6 A-6 C-13 1.44 −1.60Example 2-7 A-6 C-14 1.52 −1.66 Example 2-8 A-6 C-15 1.39 −1.71Comparative A-6 D-1 0.98 −0.88 Example 2-2 Comparative A-6 D-2 1.09−0.95 Example 2-3 Comparative A-7 B 0.98 −0.12 Example 2-4 Example 2-9A-7 C-1 1.42 −1.81 Example 2-10 A-7 C-3 1.39 −1.57 Example 2-11 A-7 C-51.45 −1.73 Example 2-12 A-7 C-6 1.44 −1.64 Example 2-13 A-7 C-12 1.54−1.78 Example 2-14 A-7 C-13 1.59 −1.75 Example 2-15 A-7 C-14 1.61 −1.74Example 2-16 A-7 C-15 1.63 −1.65 Comparative A-7 D-1 1.03 −0.85 Example2-5 Comparative A-7 D-2 1.08 −1.07 Example 2-6

As is clear from the foregoing results, the devices of the invention arehigh in the external quantum efficiency and low in the driving voltageas compared with the comparative devices.

Comparative Example 3-1

A washed ITO substrate was put into a vapor deposition apparatus; copperphthalocyanine was vapor deposited thereon in a thickness of 10 nm; andNPD ((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 40 nm. Compound A-8 and CBP(4,4′-di(9-carbazoyl)biphenyl) were vapor deposited thereon at a ratioof 12/88 (mass ratio) in a thickness of 15 nm, thereby fabricating alight emitting layer. BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of40 nm (electron transport layer). After vapor depositing thereon lithiumfluoride in a thickness of 3 nm, aluminum was vapor deposited in athickness of 60 nm to prepare a device. The EL device was subjected tolight emission upon being impressed with a direct current constantvoltage using a source measure unit MODEL 2400, manufactured by ToyoCorporation. As a result, phosphorescence derived from the Compound A-8was obtained.

Examples 3-1 to 3-6 and Comparative Examples 3-2 to 3-3

Devices were prepared in the same manner as in Comparative Example 3-1,except for changing the compound used in the light emitting layer to acompound shown in Table 3 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 3.

TABLE 3

Difference External in driving quantum voltage from Light efficiencyComparative emitting (relative Example layer value) 3-1 (ΔV) ComparativeA-8 CBP 1.00 — Example 3-1 Example 3-1 A-8 C-1 1.25 −1.33 Example 3-2A-8 C-3 1.21 −1.28 Example 3-3 A-8 C-5 1.39 −1.66 Example 3-4 A-8 C-61.38 −1.55 Example 3-5 A-8 C-9 1.50 −1.67 Example 3-6 A-8 C-10 1.42−1.51 Comparative A-8 D-1 1.04 −0.78 Example 3-2 Comparative A-8 D-21.09 −0.84 Example 3-3

As is clear from the foregoing results, the devices of the invention arehigh in the external quantum efficiency and low in the driving voltageas compared with the comparative devices.

Comparative Example 4-1

A washed ITO substrate was put into a vapor deposition apparatus; copperphthalocyanine was vapor deposited thereon in a thickness of 10 nm; andNPD ((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 40 nm. Rubrene and Compound D-1 werevapor deposited thereon at a ratio of 3/97 (mass ratio) in a thicknessof 10 nm, thereby fabricating a light emitting layer. BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of40 nm (electron transport layer). After vapor depositing thereon lithiumfluoride in a thickness of 3 nm, aluminum was vapor deposited in athickness of 60 nm to prepare a device. The EL device was subjected tolight emission upon being impressed with a direct current constantvoltage using a source measure unit MODEL 2400, manufactured by ToyoCorporation. As a result, phosphorescence derived from rubrene wasobtained.

Examples 4-1 to 4-3

Devices were prepared in the same manner as in Comparative Example 4-1,except for changing the compound used in the light emitting layer to acompound shown in Table 4 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 4.

TABLE 4 Rubrene

Difference External in driving quantum voltage from Light efficiencyComparative emitting (relative Example layer value) 4-1 (ΔV) ComparativeRubrene D-1 1.00 — Example 4-1 Example 4-1 Rubrene C-10 1.56 −1.56Example 4-2 Rubrene C-9 1.77 −1.63 Example 4-3 Rubrene C-1 1.65 −1.86

As is clear from the foregoing results, the devices of the invention arehigh in the external quantum efficiency and low in the driving voltageas compared with the comparative devices.

Comparative Example 5-1

Similar to Comparative Example 1-1, a washed ITO substrate was put intoa vapor deposition apparatus; copper phthalocyanine was vapor depositedthereon in a thickness of 10 nm; and NPD((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 37 nm. Compound D-1 was vapordeposited thereon in a thickness of 3 mm. Compound A-1 and Compound Bwere vapor deposited thereon at a ratio of 12/88 (mass ratio) in athickness of 20 nm, thereby fabricating a light emitting layer. BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of40 nm (electron transport layer). After vapor depositing thereon lithiumfluoride in a thickness of 3 nm, aluminum was vapor deposited in athickness of 60 nm to prepare a device. The EL device was subjected tolight emission upon being impressed with a direct current constantvoltage using a source measure unit MODEL 2400, manufactured by ToyoCorporation. As a result, phosphorescence derived from the Compound A-1was obtained.

Examples 5-1 to 5-3

Devices were prepared in the same manner as in Comparative Example 5-1,except for changing the compound used in the light emitting layer to acompound shown in Table 5 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 5.

TABLE 5 Difference in External driving voltage Hole Light quantum fromComparative transport emitting efficiency Example 5-1 layer layer(relative value) (ΔV) Comparative D-1 A-1 B 1.00 — Example 5-1 Example5-1 C-1 A-1 B 1.05 −0.52 Example 5-2 C-9 A-1 B 1.22 −1.38 Example 5-3C-10 A-1 B 1.23 −0.96

As is clear from the foregoing Examples, it was noted that the devicesof the invention containing the compound represented by the formula (1)in the layer (hole transport layer) adjacent to the light emitting layeron the side close to the anode are able to enhance the external quantumefficiency of the electroluminescence device and to achieve low-voltagedriving.

Comparative Example 6-1

Similar to Comparative Example 1-1, a washed ITO substrate was put intoa vapor deposition apparatus; copper phthalocyanine was vapor depositedthereon in a thickness of 10 nm; and NPD((N,N′-di-α-naphthyl-N,N′-diphenyl)-benzidine) was further vapordeposited thereon in a thickness of 40 nm. Compound A-1 and Compound Bwere vapor deposited thereon at a ratio of 12/88 (mass ratio) in athickness of 20 nm, thereby fabricating a light emitting layer. CompoundD-2 was vapor deposited thereon in a thickness of 10 nm. BAlq[bis-(2-methyl-8-quinolinolate)-4-(phenylphenolate)aluminum][bis(6-hydroxyquinoline)-4-(phenyl-phenol)Al complex salt] was further vapor deposited thereon in a thickness of30 nm (electron transport layer). After vapor depositing thereon lithiumfluoride in a thickness of 3 nm, aluminum was vapor deposited in athickness of 60 nm to prepare a device. The EL device was subjected tolight emission upon being impressed with a direct current constantvoltage using a source measure unit MODEL 2400, manufactured by ToyoCorporation. As a result, phosphorescence derived from the Compound A-1was obtained.

Examples 6-1 to 6-3

Devices were prepared in the same manner as in Comparative Example 6-1,except for changing the compound used in the light emitting layer to acompound shown in Table 6 and then evaluated. As a result,phosphorescence derived from each of the used light emitting materialswas obtained. The obtained results are summarized in Table 6.

TABLE 6 Difference in External driving voltage Light Electron quantumfrom Comparative emitting transport efficiency Example 6-1 layer layer(relative value) (ΔV) Comparative A-1 B D-1 1.00 — Example 6-1 Example6-1 A-1 B C-5 1.14 −0.89 Example 6-2 A-1 B C-6 1.28 −1.21 Example 6-3A-1 B C-10 1.19 −1.07

As is clear from the foregoing Examples, it was noted that the devicesof the invention containing the compound represented by the formula (1)in the layer (electron transport layer) adjacent to the light emittinglayer on the side close to the cathode are able to enhance the externalquantum efficiency of the electroluminescence device and to achievelow-voltage driving.

The organic electroluminescence device of the invention is characterizedin that at least one of the compounds represented by the formula (1) iscontained in the organic compound layer. According to this, an organicelectroluminescence device (synonymous with the “device of theinvention” in this specification) having high luminous efficiency (forexample, external quantum efficiency) and capable of being driven at alow voltage may be provided.

The entire disclosure of each and every foreign patent application fromwhich the benefit of foreign priority has been claimed in the presentapplication is incorporated herein by reference, as if fully set forth.

1. An organic electroluminescence device, comprising: a pair ofelectrodes; and at least one organic layer including a light emittinglayer, the light emitting layer being provided between the pair ofelectrodes, wherein at least one layer of the at least one organic layercontains a compound represented by formula (1):

wherein each of Z₁₁ and Z₁₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring; R₁₁ represents ahydrogen atom or a substituent, provided that a plurality of R₁₁s arethe same or different; m represents an integer of 1 or more; and L₁represents a single bond or an m-valent linking group and is linked toany one of C atoms in R₁₁, Z₁₁ and Z₁₂, provided that when m is 1, L₁does not exist.
 2. The organic electroluminescence device according toclaim 1, wherein the compound represented by formula (1) is a compoundrepresented by formula (2):

wherein Z₂₂ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring; R₂₁ represents a hydrogen atom or a substituent,provided that a plurality of R₂₁s are the same or different; each of A₂₁to A₂₃ independently represents a nitrogen atom or C—R₂₂; R₂₂ representsa hydrogen atom or a substituent, provided that a plurality of R₂₂s arethe same or different; m represents an integer of 1 or more; and L₂represents a single bond or an m-valent linking group and is linked toany one of C atoms in R₂₁, Z₂₂ and A₂₁ to A₂₃, provided that when m is1, L₂ does not exist.
 3. The organic electroluminescence deviceaccording to claim 1, wherein the compound represented by formula (1) isa compound represented by formula (3):

wherein Z₃₁ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring; R₃₁ represents a hydrogen atom or a substituent,provided that a plurality of R₃₁s are the same or different; each of A₃₁to A₃₄ independently represents a nitrogen atom or C—R₃₂; R₃₂ representsa hydrogen atom or a substituent, provided that a plurality of R₃₂s arethe same or different; m represents an integer of 1 or more; and L₃represents a single bond or an m-valent linking group and is linked toany one of C atoms in R₃₁, Z₃₁ and A₃₁ to A₃₄, provided that when m is1, L₃ does not exist.
 4. The organic electroluminescence deviceaccording to claim 2, wherein the compound represented by formula (2) isa compound represented by formula (4):

wherein R₄₁ represents a hydrogen atom or a substituent, provided that aplurality of R₄₁s are the same or different; each of A₄₁ to A₄₇independently represents a nitrogen atom or C—R₄₂; R₄₂ represents ahydrogen atom or a substituent, provided that a plurality of R₄₂s arethe same or different; m represents an integer of 1 or more; and L₄represents a single bond or an m-valent linking group and is linked toany one of C atoms in R₄₁ and A₄₁ to A₄₇, provided that when m is 1, L₄does not exist.
 5. The organic electroluminescence device according toclaim 1, wherein the compound represented by formula (1) is a compoundrepresented by formula (5):

wherein each of Z₅₁ to Z₅₃ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring; m represents aninteger of 1 or more; and L₅ represents a single bond or an m-valentlinking group and is linked to any one of C atoms in Z₅₁ to Z₅₃,provided that when m is 1, L₅ does not exist.
 6. The organicelectroluminescence device according to claim 5, wherein the compoundrepresented by the formula (5) is a compound represented by formula (6):

wherein each of Z₆₁ and Z₆₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring; each of A₆₁ to A₆₃independently represents a nitrogen atom or C—R₆₁; R₆₁ represents ahydrogen atom or a substituent, provided that a plurality of R₆₁s arethe same or different; m represents an integer of 1 or more; and L₆represents a single bond or an m-valent linking group and is linked toany one of C atoms in Z₆₁, Z₆₂ and A₆₁ to A₆₃, provided that when m is1, L₆ does not exist.
 7. The organic electroluminescence deviceaccording to claim 6, wherein the compound represented by the formula(6) is a compound represented by formula (8):

wherein Z₈₂ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring; each of A₈₁ to A₈₇ independently represents a nitrogenatom or C—R₈₁; R₈₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₈₁s are the same or different; m represents aninteger of 1 or more; and L₈ represents a single bond or an m-valentlinking group and is linked to any one of C atoms in Z₈₂ and A₈₁ to A₈₇,provided that when m is 1, L₈ does not exist.
 8. The organicelectroluminescence device according to claim 7, wherein the compoundrepresented by the formula (8) is a compound represented by formula(10):

wherein each of A₁₀₁ to A₁₀₁₁ independently represents a nitrogen atomor C—R₁₀₁; R₁₀₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₁₀₁s are the same or different; m represents aninteger of 1 or more; and L₁₀ represents a single bond or an m-valentlinking group and is linked to any one of C atoms in A₁₀₁ to A₁₀₁₁,provided that when m is 1, L₁₀ does not exist.
 9. The organicelectroluminescence device according to claim 5, wherein the compoundrepresented by formula (5) is a compound represented by formula (7):

wherein each of Z₇₁ and Z₇₂ independently represents an aromaticheterocyclic ring or an aromatic hydrocarbon ring; each of A₇₁ to A₇₄independently represents a nitrogen atom or C—R₇₁; R₇₁ represents ahydrogen atom or a substituent, provided that a plurality of R₇₁s arethe same or different; m represents an integer of 1 or more; and L₇represents a single bond or an m-valent linking group and is linked toany one of C atoms in Z₇₁, Z₇₂ and A₇₁ to A₇₄, provided that when m is1, L₇ does not exist.
 10. The organic electroluminescence deviceaccording to claim 9, wherein the compound represented by the formula(7) is a compound represented by formula (9):

wherein Z₉₁ represents an aromatic heterocyclic ring or an aromatichydrocarbon ring; each of A₉₁ to A₉₈ independently represents a nitrogenatom or C—R₉₁; R₉₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₉₁s are the same or different; m represents aninteger of 1 or more; and L₉ represents a single bond or an m-valentlinking group and is linked to any one of C atoms in Z₉₁ and A₉₁ to A₉₈,provided that when m is 1, L₉ does not exist.
 11. The organicelectroluminescence device according to claim 1, wherein the lightemitting layer contains the compound represented by formula (1).
 12. Theorganic electroluminescence device according to claim 1, wherein thepair of electrodes includes an anode, a hole transport layer is providedbetween the light emitting layer and the anode, and the hole transportlayer contains the compound represented by formula (1).
 13. The organicelectroluminescence device according to claim 1, wherein the pair ofelectrodes includes a cathode, an electron transport layer is providedbetween the light emitting layer and the cathode, and the electrontransport layer contains the compound represented by formula (1). 14.The organic electroluminescence device according to claim 1, wherein aglass transition temperature of the compound represented by formula (1)is 130° C. or higher and not higher than 450° C.
 15. The organicelectroluminescence device according to claim 1, wherein a minimumexcitation triplet energy level of the compound represented by formula(1) is 60 kcal/mole (251.4 kJ/mole) or more and not more than 95kcal/mole (398.1 kJ/mole).
 16. A compound represented by formula (4-1):

wherein each of X₄₁₁ and X₄₁₂ independently represents C—R₄₁₁; R₄₁₁represents a hydrogen atom or a substituent, provided that a pluralityof R₄₁₂s are the same or different; each of A₄₁₁ to A₄₁₇ independentlyrepresents a nitrogen atom or C—R₄₁₂; R₄₁₂ represents a hydrogen atom ora substituent, provided that a plurality of R₄₁₂s are the same ordifferent; L₄₁ represents a single bond or an m-valent linking group andis linked to any one of C atoms in X₄₁₁, X₄₁₂ and A₄₁₁ to A₄₁₇; when thelinking group as L₄₁ is an aromatic hydrocarbon ring group or anaromatic heterocyclic group, a size of the ring is from a 5-membered to6-membered ring; and m represents an integer of 2 or more.
 17. Thecompound according to claim 16, which is a compound represented byformula (4-2):

wherein each of X₄₂₁ and X₄₂₂ independently represents C—R₄₂₁; R₄₂₁represents a hydrogen atom or a substituent, provided that a pluralityof R₄₂₁s are the same or different; each of A₄₂₁ to A₄₂₇ independentlyrepresents a nitrogen atom or C—R₄₂₂; R₄₂₂ represents a hydrogen atom ora substituent, provided that a plurality of R₄₂₂s are the same ordifferent; R₄₂₃ represents a hydrogen atom or a substituent, providedthat a plurality of R₄₂₃s are the same or different; m represents aninteger of from 2 to 4; and the silicon linking group is linked to anyone of C atoms in X₄₂₁, X₄₂₂ and A₄₂₁ to A₄₂₇.
 18. The compoundaccording to claim 16, which is a compound represented by formula (4-3):

wherein each of X₄₃₁ and X₄₃₂ independently represents C—R₄₃₁; R₄₃₁represents a hydrogen atom or a substituent, provided that a pluralityof R₄₃₁s are the same or different; each of A₄₃₁ to A₄₃₇ independentlyrepresents a nitrogen atom or C—R₄₃₂; R₄₃₂ represents a hydrogen atom ora substituent, provided that a plurality of R₄₃₂s are the same ordifferent; R₄₃₃ represents a hydrogen atom or a substituent, providedthat a plurality of R₄₃₃s are the same or different; m represents aninteger of from 2 to 4; and the carbon linking group is linked to anyone of C atoms in X₄₃₁, X₄₃₂ and A₄₃₁ to A₄₃₇.
 19. The compoundaccording to claim 16, which is a compound represented by formula (4-4):

wherein each of X₄₄₁ and X₄₄₂ independently represents C—R₄₄₁; R₄₄₁represents a hydrogen atom or a substituent, provided that a pluralityof R₄₄₁s are the same or different; each of A₄₄₁ to A₄₄₇ independentlyrepresents a nitrogen atom or C—R₄₄₂; R₄₄₂ represents a hydrogen atom ora substituent, provided that a plurality of R₄₄₂s are the same ordifferent; Ar₄₄ represents an aromatic hydrocarbon ring or an aromaticheterocyclic ring, and a size of the ring is from 5-membered to6-membered ring; Ar₄₄ is linked to any one of C atoms in X₄₄₁, X₄₄₂ andA₄₄₁ to A₄₄₇; R₄₄₃ represents a hydrogen atom or a substituent, providedthat a plurality of R₄₄₃s are the same or different; m represents aninteger of 2 or more; and n represents an integer of 0 or more.
 20. Thecompound according to claim 16, which is a compound represented byformula (10-1):

wherein each of A₁₀₁₁ to A₁₀₁₁₁ independently represents a nitrogen atomor C—R₁₀₁₁; R₁₀₁₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₁₀₁₁ are the same or different; L₁₀₁ represents asingle bond or an m-valent linking group and is linked to any one of Catoms in A₁₀₁₁ to A₁₀₁₁₁; when the linking group as L₁₀₁ is an aromatichydrocarbon ring group or an aromatic heterocyclic group, a size of thering is from a 5-membered to 6-membered ring; and m represents aninteger of 2 or more.
 21. The compound according to claim 20, which is acompound represented by formula (10-2):

wherein each of A₁₀₂₁ to A₁₀₂₁ independently represents a nitrogen atomor C—R₁₀₂₁; R₁₀₂₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₁₀₂₁s are the same or different; R₁₀₂₂ represents ahydrogen atom or a substituent, provided that a plurality of R₁₀₂₂s arethe same or different; m represents an integer of from 2 to 4; and thesilicon linking group is linked to any one of C atoms in A₁₀₂₁ toA₁₀₂₁₁.
 22. The compound according to claim 20, which is a compoundrepresented by formula (10-3):

wherein each of A₁₀₃₁ to A₁₀₃₁₁ independently represents a nitrogen atomor C—R₁₀₃₁; R₁₀₃₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₁₀₃₁s are the same or different; R₁₀₃₂ represents ahydrogen atom or a substituent, provided that a plurality of R₁₀₃₂s arethe same or different; m represents an integer of from 2 to 4; and thecarbon linking group is linked to any one of C atoms in A₁₀₃₁ to A₁₀₃₁₁.23. The compound according to claim 20, which is a compound representedby formula (10-4):

wherein each of A₁₀₄₁ to A₁₀₄₁₁ independently represents a nitrogen atomor C—R₁₀₄₁; R₁₀₄₁ represents a hydrogen atom or a substituent, providedthat a plurality of R₁₀₄₁s are the same or different; Ar₁₀₄ representsan aromatic hydrocarbon ring or an aromatic heterocyclic ring, and asize of the ring is from 5-membered to 6-membered ring; Ar₁₀₄ is linkedto any one of C atoms in A₁₀₄₁ to A₁₀₄₁₁; R₁₀₄₂ represents a hydrogenatom or a substituent, provided that a plurality of R₁₀₄₂s are the sameor different; m represents an integer of 2 or more; and n represents aninteger of 0 or more.
 24. An organic electroluminescence device,comprising: a pair of electrodes; and at least one organic layerincluding a light emitting layer, the light emitting layer beingprovided between the pair of electrodes, wherein at least one layer ofthe at least one organic layer contains the compound represented byformula (4-1) according to claim
 16. 25. The organic electroluminescencedevice according to claim 24, wherein the light emitting layer containsa phosphorescent material.
 26. The organic electroluminescence deviceaccording to claim 25, wherein the phosphorescent material is an iridiumcomplex or a platinum complex.
 27. An organic electroluminescencedevice, comprising: a pair of electrodes; and at least one organic layerincluding a light emitting layer, the light emitting layer beingprovided between the pair of electrodes, wherein at least one layer ofthe at least one organic layer contains the compound represented byformula (10-1) according to claim 20.